Halogen Bonded Directly To The Benzene Ring Patents (Class 568/656)
  • Patent number: 4873018
    Abstract: An optically active 2-fluoro-1-alkanol compound represented by the formula (Ia): ##STR1## wherein R is an alkyl group having 1-16 carbon atoms, and C* is an asymmetric carbon atom; and an optically active compound derived from the fluoroalkanol and represented by the formula (Ib): ##STR2## wherein R and C* are the same as above, m is 1 or 2, n is 0 or 1, and A is a releasable substitutent. Because of the fluorine atom directly attached to an asymmetric carbon atom, these compounds are particularly effective in increasing a spontaneous polarization, improving a electric field responsive characteristic of a liquid crystal composition, and controlling the liquid crystal state.
    Type: Grant
    Filed: October 27, 1987
    Date of Patent: October 10, 1989
    Assignees: Canon Kabushiki Kaisha, Yamakawa Yakuhin Kogyo Kabushiki Kaisha
    Inventors: Hiroyuki Nohira, Masanao Kamei, Shinichi Nakamura, Kazuo Yoshinaga, Mariko Kai, Kazuharu Katagiri
  • Patent number: 4828764
    Abstract: N-fluoro-N-perfluoromethyl sulfonamide compounds are provided as fluorinating agents for the fluorination of organic compounds by either the direct electrophilic fluorination of organic compounds or by the fluorination of organic compound carbanions.
    Type: Grant
    Filed: June 18, 1987
    Date of Patent: May 9, 1989
    Assignee: Research Corporation
    Inventor: Darryl D. DesMarteau
  • Patent number: 4822927
    Abstract: Disclosed is a process for continuous preparation of aromatic fluorides wherein aromatic diazonium fluorides are continuously decomposed at low concentration in a reaction system of one or more continuous agitated reactors.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: April 18, 1989
    Assignee: Mallinckrodt, Inc.
    Inventors: Nickolas J. Stepaniuk, Bruce J. Lamb
  • Patent number: 4816596
    Abstract: A process for preparing substituted or unsubstituted trifluoroethoxy- or trifluoroethylthiobenzenes by reaction of a phenol or thiophenol, both of which may be substituted or unsubstituted, with a compound of the formula CF.sub.3 --CH.sub.2 --O--R', where R' is a moiety selected from the group consisting of trifluoroacetyl, methanesulfonyl, paratoluenesulfonyl, trichloromethanesulfonyl and chlorosulfonyl, in the presence of a strong alkaline base and a complexing agent of the formula:N--CHR.sub.1 --CHR.sub.2 --O--(CHR.sub.3 --CHR.sub.4 --O).sub.n --R.sub.5 ].sub.3 (II)wherein n is an integer from 0 to 10 (0 is less than or equal to n is less than or equal to 10), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, are selected from the group consisting of a hydrogen atom and an alkyl moiety having from 1 to 4 carbon atoms, and R.sub.5 denotes an alkyl or cycloalkyl moiety having from 1 to 12 carbon atoms, a phenyl moiety or a moiety of the formula: --C.sub.m H.sub.2m --C.sub.6 H.sub.
    Type: Grant
    Filed: March 28, 1986
    Date of Patent: March 28, 1989
    Assignee: Rhone-Polenc Specialites Chimoues
    Inventor: Bernard Langlois
  • Patent number: 4783285
    Abstract: The nucleophilic substitution upon unactivated monocyclic or polycyclic aromatic or heteroaromatic substrates bearing suitable leaving groups can be achieved by catalyzing the substitution of said leaving groups by an anionic nucleophile with a cyclic or acyclic polydentate chelating ligand. Specific products of this reaction can be used in preparing sulfonylurea herbicides.
    Type: Grant
    Filed: February 3, 1987
    Date of Patent: November 8, 1988
    Assignee: E. I. DuPont de Nemours and Company
    Inventor: Alden D. Josey
  • Patent number: 4766243
    Abstract: A process for the electrophilic ring fluorination of aromatic compounds which comprises reacting a fluorinating agent from the group consisting of CF.sub.3 OF and CF.sub.2 (OF).sub.2 with an aromatic compound of the formula ##STR1## where X is selected from the group consisting of ##STR2## and ##STR3## and Y is selected from the group consisting of --H, --CF.sub.3, --CN, --NO.sub.2, --Cl, and CH.sub.3.
    Type: Grant
    Filed: August 10, 1984
    Date of Patent: August 23, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Michael J. Fifolt
  • Patent number: 4740630
    Abstract: A chiral phenylether compound having the formula ##STR1## wherein X is a halogen atom; m is an integer from 3 to 5, n is an integer from 3 to 12 and * designates an asymmetric carbon is disclosed. The chiral phenylether compounds are useful to prepare chiral smectic phase pyrimidine phenylether liquid crystal compounds of the formula. ##STR2## The reaction is carried by reacting (I) with butylithium, dissolving in ether and reacting with a 1-bromoalkane to yield (IV). Compounds (IV) are particularly well suited to broaden the useful temperature range of ferroelectric liquid crystal materials.
    Type: Grant
    Filed: December 19, 1986
    Date of Patent: April 26, 1988
    Assignee: Seiko Epson Corporation
    Inventors: Yoshio Shionozaki, Toshihiro Shibata
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4730046
    Abstract: A process for selectively substituting an aromatic nitro group with a halo group which comprises contacting the nitroaromatic compound with a phosphorushalide of formula: R.sub.n PX.sub.5-n wherein n is selected from 0, 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of: straight and branched chain alkyl, alkoxy, and haloalkyl; halogen, sulfonate and mixtures thereof; and X is a halogen in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphosphorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture to maintain a temperature of from about 100.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: April 14, 1986
    Date of Patent: March 8, 1988
    Assignee: Stauffer Chemical Company
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4727187
    Abstract: The present invention relates to a novel process for the preparation of an .alpha.,.alpha.-difluoroalkyl phenyl ether of formula I ##STR1## wherein R.sup.1 is hydrogen, halogen, amino, nitro, --SO.sub.2 --R.sup.4, --S--R.sup.5, --SO--R.sup.6 or --S--S--R.sup.7,R.sup.2 is hydrogen, halogen, nitro, hydroxy or --SO.sub.2 --R.sup.8,R.sup.3 is C.sub.1 -C.sub.5 haloalkyl,X is oxygen, sulfur, --SO-- or --SO.sub.2 --,R.sup.4 is hydroxy, halogen, amino, --N.dbd.C.dbd.O, --NH--CO--Cl, --NH--CO--Br, --NR.sup.9 R.sup.10, benzyl, phenyl, C.sub.1 -C.sub.4 alkyl or --NH'CO--NR.sup.11 R.sup.12,R.sup.5 and R.sup.6 are C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.7 is C.sub.1 -C.sub.4 alkyl, phenyl or benzyl,R.sup.8 is hydroxy or halogen,R.sup.9 and R.sup.10 are each independently of the other C.sub.1 -C.sub.4 alkyl or benzyl andR.sup.11 and R.sup.12 are each independently of the other hydrogen, C.sub.1 -C.sub.
    Type: Grant
    Filed: June 5, 1985
    Date of Patent: February 23, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Urs Siegrist, Jean Indermuhle, Peter Baumeister
  • Patent number: 4724269
    Abstract: A process for producing a p-chlorobenzene having the formula: ##STR1## wherein R is a lower alkyl group, a lower alkoxy group or a halogen atom, which comprises chlorinating a benzene having the formula: ##STR2## wherein R is as defined above, in a liquid phase in the presence of a catalyst, characterized in that the catalyst is a combination of an aliphatic alcohol having the formula:R'OH (III)wherein R' is a lower alkyl group or a lower haloalkyl group, and a zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 3 to 8 and a pore size of from 6 to 10 .ANG..
    Type: Grant
    Filed: June 18, 1986
    Date of Patent: February 9, 1988
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Toshihiro Suzuki, Chizu Komatsu
  • Patent number: 4695657
    Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: September 22, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4683091
    Abstract: The nucleophilic substitution upon unactivated monocyclic or polycyclic aromatic or heteroaromatic substrates bearing suitable leaving groups can be achieved by catalyzing the substitution of said leaving groups by an anionic nucleophile with a cyclic or acyclic polydentate chelating ligand. Specific products of this reaction can be used in preparing sulfonylurea herbicides.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: July 28, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Alden D. Josey
  • Patent number: 4678811
    Abstract: New substituted benzyl-type ethers of formula I ##STR1## in which R.sub.1 is aryl or aryl substituted by C.sub.1-4 -alkyl, halo-C.sub.1-4 -alkyl, phenyl-C.sub.1-4 -alkyl, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.sub.2-4 -alkenyl, C.sub.2-4 -alkynyl, halo-C.sub.2-4 -alkynyl, phenyl-C.sub.2-4 -alkynyl, C.sub.1-4 -alkoxy, halo-C.sub.1-4 -alkoxy, phenyl-C.sub.1-4 -alkoxy, C.sub.2-4 -alkenyloxy, halo-C.sub.2-4 -alkenyloxy, phenyl-C.sub.2-4 -alkenyloxy, C.sub.2-4 -alkynyloxy, halo-C.sub.2-4 -alkynyloxy, phenyl-C.sub.2-4 -alkynyloxy, alkylsulfonyloxy, haloalkylsulfonyloxy, arylsulfonyloxy, halo, cyano, nitro, aryloxy, haloaryloxy, C.sub.1-4 -alkyl-aryloxy, or nitroaryloxy,R.sub.2 is hydrogen or C.sub.1-4 alkyl,R.sub.3 is hydrogen, cyano or ethynyl,R.sub.4 is phenyl or pyridyl or one of these groups substituted by one or more of C.sub.1-6 -alkyl, halo-C.sub.1-6 -alkyl, phenyl-C.sub.1-6 -alkyl, C.sub.1-6 -alkyl interrupted by an O--, N-- or S-- atom, C.sub.2-4 -alkenyl, halo-C.sub.2-4 -alkenyl, phenyl-C.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 7, 1987
    Assignee: Schering Aktiengesellschaft
    Inventors: Helga Franke, Heinrich Franke, Hans-Rudolf Kruger, Hartmut Joppien
  • Patent number: 4668830
    Abstract: A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group.The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: May 26, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4654446
    Abstract: Alkylarylethers are produced according to the invention using phenols and ethers of aliphatic alcohols as the starting materials, in the presence of BPO.sub.4.
    Type: Grant
    Filed: February 27, 1986
    Date of Patent: March 31, 1987
    Assignee: Eniricerche S.p.A.
    Inventors: Maurizio Brunelli, Pierferdinando Ferrari, Fabrizio Stroppa, Giuseppe Bellussi
  • Patent number: 4650910
    Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.
    Type: Grant
    Filed: March 4, 1986
    Date of Patent: March 17, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
  • Patent number: 4642349
    Abstract: Aromatic ethers or polyethers are prepared by reacting an organic halide such as a hydrocarbon halide with an aryl lower alkyl carbonate in the presence of an initiator.
    Type: Grant
    Filed: May 24, 1982
    Date of Patent: February 10, 1987
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga
  • Patent number: 4629814
    Abstract: This process relates to the preparation of unsubstituted or substituted bis-bromoalkyl ethers by reacting unsubstituted or substituted 1,3-dioxolane or unsubstituted or substituted 1,3-dioxane with thionyl bromide. The bis-bromoalkyl ethers made by this process can be used in preparing biologically active compounds.
    Type: Grant
    Filed: August 27, 1985
    Date of Patent: December 16, 1986
    Assignee: Rohm and Haas Company
    Inventor: Michael P. James
  • Patent number: 4621095
    Abstract: The invention relates to bis-azolyl-substituted t-butanol derivatives defined herein under formula (I) and their use as antimycotic agents. Included in the invention are compositions containing said t-butanol derivatives and methods for using said derivatives and compositions containing them for their antimycotic activity.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: November 4, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erik Regel, Karl H. Buchel, Manfred Plempel
  • Patent number: 4621160
    Abstract: A process for the chlorination of aromatic derivatives. The aromatic derivative is reacted with chlorine gas in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: November 4, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4620040
    Abstract: Trifluoroanisoles of the formula ##STR1## where m is 1 or 2 and n is 0 to 3, are prepared by reacting hydrogen fluoride with trichloroanisoles of the formula ##STR2## in the vapor phase, in the presence of a fluorinated alumina catalyst whereinX is halogen other than fluorine;R is aryl, preferably 1 to 14 carbon atoms, halogen substituted aryl, halogen, alkyl of 1 to 6 carbon atoms, or alkoxy of 1 to 6 carbon atoms;m is 1 or 2;n is 0 to 3;w is 0 to 2;p is 1 to 3;q is 0 to 2;w+p+q is 3;w' is 1 to 3 and is greater than w;p' is 0 to 2 and is less than p;q' is 0 to 2 and is equal to q; andw'+p'+q' is 3.
    Type: Grant
    Filed: March 18, 1985
    Date of Patent: October 28, 1986
    Assignee: Occidental Chemical Corporation
    Inventor: Derek J. Alsop
  • Patent number: 4607128
    Abstract: Novel compounds of the general formula ##STR1## in which X is hydrogen or chlorine, and each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently is hydrogen, methyl or ethyl, are useful intermediates in the preparation of the corresponding phenols. They may be prepared by treating a compound of the formula ##STR2## in which Hal is chlorine or fluorine, with a compound of the formulaHO--CHR.sup.1 --CR.sup.2 .dbd.CR.sup.3 R.sup.4in the presence of a base.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: August 19, 1986
    Assignee: Shell Oil Company
    Inventors: Paul H. Briner, Ronald F. Mason
  • Patent number: 4598085
    Abstract: Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.
    Type: Grant
    Filed: January 21, 1982
    Date of Patent: July 1, 1986
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Jan Heeres, Leo J. J. Backx, Joseph A. Mostmans
  • Patent number: 4582948
    Abstract: Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0, 1 or 2; n is 0, 1 or 2; q is 1 or 2; q+m+n is less than 6; and when q is 1, m is 2; are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, n and q are as defined above.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: April 15, 1986
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4567280
    Abstract: In a process for producing an iodo-aromatic compound which comprises iodinating an aromatic compound having an electron-donating substituent bonded to the benzene ring with iodine in the presence of a solvent, the improvement wherein about 1/2 to about 10 moles, per mole of iodine added to the reaction system, of nitrogen dioxide (NO.sub.2) is added in the form of NO.sub.2 to the reaction system, and the reaction is carried out in the presence of nitrogen dioxide.
    Type: Grant
    Filed: September 4, 1984
    Date of Patent: January 28, 1986
    Assignee: UBE Industries, Ltd.
    Inventors: Hiroshi Itatani, Mikito Kashima, Yasutaka Tasaki
  • Patent number: 4558166
    Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.
    Type: Grant
    Filed: March 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Erich Klauke
  • Patent number: 4542243
    Abstract: The present invention relates to a process for producing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl ethers having excellent insecticidal and acaricidal activities which are represented by formula (IV): ##STR1## wherein R is a lower alkyl group and X.sub.1 and X.sub.2 are each a hydrogen or fluorine atom, which comprises reacting a 3-halogeno-4-alkoxyneophyl halide represented by the formula (I): ##STR2## wherein Y.sub.1 and Y.sub.2 are each a hydrogen, chlorine or bromine atom, at least one of them being a chlorine or bromine atom, R has the same meaning as above and X is a halogen atom, with a 3-phenoxybenzyl alcohol represented by the formula (II): ##STR3## wherein X.sub.1 and X.sub.2 have the same meaning as above, in the presence of a base to obtain a 3-phenoxybenzyl 2-(4-alkoxy-3-halogenophenyl)-2-methylpropyl ether represented by the formula (III): ##STR4## wherein Y.sub.1, Y.sub.2, R, X.sub.1 and X.sub.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mitsumasa Umemoto, Tamotsu Asano, Teruyuki Nagata, Satoshi Numata
  • Patent number: 4538003
    Abstract: Process for the monoalkylation/monoarylation of dihaloaromatic compounds by treating the latter with selected magnesium or zinc organometallic reagents in the presence of a nickel/bidentate or tridentate phosphorus ligand. The products are intermediates to agricultural and pharmaceutical compounds.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: August 27, 1985
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Wilson Tam
  • Patent number: 4524032
    Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: June 18, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
  • Patent number: 4518808
    Abstract: Disclosed is a process for the preparation of certain dichloro-hydroxy and alkoxy aromatic compounds by reacting the corresponding unchlorinated compound with sulfuryl chloride in the presence of acetic acid, propionic acid or lower alkyl esters thereof.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: May 21, 1985
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Garry L. Myers
  • Patent number: 4507492
    Abstract: Allyl derivatives of phenols, thiophenols and arylamines are prepared by contacting such aromatic reactant with an allyl lower alkyl carbonate in the presence of a molybdenum, tungsten or Group VIII metal.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: March 26, 1985
    Assignee: The Dow Chemical Company
    Inventor: Edmund P. Woo
  • Patent number: 4495353
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4470930
    Abstract: Chloro-aromatic compounds of the formula ##STR1## wherein R is CF.sub.3, OCF.sub.3, OC.sub.2 F.sub.5, CN, NCO, or COCl, m is 0 or 1, and n is 0 or 1 are prepared by the vapor phase chloro-denitration reaction of a chlorinating agent with a nitro-aromatic compound of the formula ##STR2## where R, m, and n are as defined above.
    Type: Grant
    Filed: February 9, 1982
    Date of Patent: September 11, 1984
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
  • Patent number: 4447660
    Abstract: Process for the isomerization of ortho- and para-bromophenols or the ethers thereof into corresponding meta-brominated derivatives by isomerizing ortho- and para-bromophenols in the corresponding ethers in the presence of a liquid superacid at a temperature in the region of ambient temperature.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: May 8, 1984
    Assignee: PCUK Produits Chimiques Ugine Kuhlmann
    Inventors: Marie-Paule Jouannetaud, Jean-Pierre Gesson, Jean-Claude Jacquessy
  • Patent number: 4429153
    Abstract: This invention relates to novel cyclopropane derivatives useful as insecticides, to processes for their preparation, to compositions comprising them and to methods of combatting insect and similar invertebrate pests using them.
    Type: Grant
    Filed: January 15, 1982
    Date of Patent: January 31, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • Patent number: 4424393
    Abstract: This invention relates to a process for preparing herbicidally active substituted diphenylethers. Also, this invention provides novel intermediates useful in the production of said diphenylethers.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: January 3, 1984
    Assignee: PPG Industries, Inc.
    Inventors: Frederick F. Guzik, Steven E. Pamer, Sidney B. Richter
  • Patent number: 4418206
    Abstract: Novel compounds of the formula: ##STR1## wherein A is CHOH, CHO or COOR; R is hydrogen or a lower alkyl group of 1 to 4 carbon atoms; and the pharmaceutically acceptable, non-toxic salts of compounds in which R is hydrogen; and X is hydrogen, o-, m- or p-halo(fluoro, chloro or bromo), o-, m- or p-methyl or o-, m- or p-methoxy. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as inhibitors of gastric acid secretions and as agents for the control of asthmatic attack, because of their bronchodilating activity.
    Type: Grant
    Filed: March 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: Douglas L. Wren
  • Patent number: 4407760
    Abstract: A method for the preparation of difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent mixture.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: October 4, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4405529
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds useful as intermediates in the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric or superatmospheric pressures in the presence of a base, water, and an inert water miscible organic solvent or solvent mixtures.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 20, 1983
    Assignee: American Cyanamid Company
    Inventors: Jack K. Siddens, Sivaraman Raghu
  • Patent number: 4404148
    Abstract: A method for the preparation of certain difluoromethoxyaromatic compounds which are useful intermediates for the preparation of pyrethroid pesticides. The method comprises alkylating a p-substituted phenol with excess chlorodifluoromethane at atmospheric and superatomspheric pressures in the presence of a base, acetone, benzyltriethylammonium chloride, and water.
    Type: Grant
    Filed: September 20, 1982
    Date of Patent: September 13, 1983
    Assignee: American Cyanamid Company
    Inventor: Jack K. Siddens
  • Patent number: 4380546
    Abstract: Azole compounds of the formula ##STR1## where X is hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, trifluoromethyl or phenyl and m is an integer from 1 to 5, and, if m is greater than 1, the X's can be identical or different, n is an integer from 2 to 5, Z is N or CH and Y is CO or CR.sup.1 OR.sup.2, where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl or C.sub.1 -C.sub.4 -alkanoyl, and their crop-tolerated addition salts with acids, and metal complexes.The compounds act as fungicides and growth regulators.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: April 19, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Hubert Sauter, Eberhard Ammermann, Costin Rentzea, Bernd Zeeh, Johann Jung, Ernst-Heinrich Pommer
  • Patent number: 4377711
    Abstract: Disclosed are aromatic bromopolyfluoroalkyl ethers of the formula: ##STR1## where n is equal to 1 or 2 and R represents at least one moiety selected from the group consisting of hydrogen, the alkyl radicals having from 1 to 12 carbon atoms, the phenyl radical, the alkoxy radicals having from 1 to 12 carbon atoms, the phenyloxy radical, and the radicals NO.sub.2, CN, Cl, F, Br, I, CF.sub.3, and CONR.sub.1 R.sub.2 and NR.sub.1 R.sub.2 where R.sub.1 and R.sub.2 are identical or different and represent each a hydrogen or an alkyl radical having from 1 to 6 carbon atoms. Also disclosed is a method for preparation of these ethers. These compounds are useful as intermediates in producing products exhibiting phytosanitary or pharmaceutical activity.
    Type: Grant
    Filed: November 4, 1981
    Date of Patent: March 22, 1983
    Assignee: Rhone-Poulenc Industries
    Inventors: Isabelle Rico, Claude Wakselman
  • Patent number: 4368135
    Abstract: Anisotropic compounds with negative or positive DCA and .DELTA.n.ltoreq.0.2 have the formula (1) ##STR1## in which R.sup.1 and R.sup.2 l are independently hydrogen, alkyl, alkoxy having 1 to 12 carbon atoms respectively, or one of R.sup.1 and R.sup.2 can represent cyclical fragment of formulae (1a) or (1b); ##STR2## the bridges Z.sup.1, Z.sup.2 and Z.sup.3 are identical or different and means covalent bonds or carboxyl or oxycarbonyl groups; R.sup.3 is hydrogen, alkyl or alkoxy group having 1 to 12 carbon atoms, respectively; X.sup.1 and X.sup.4 are independently hydrogen, halogen, nitrile or nitro, wherein at least one of X.sup.1 and X.sup.4 is not hydrogen when R.sup.2 represents a cyclical fragment of formula (1a) or (1b) and Z.sup.2 is a carboxyl group or Z.sup.3 is an oxycarbonyl group, respectively. Liquid crystal compositions are also disclosed.
    Type: Grant
    Filed: June 30, 1980
    Date of Patent: January 11, 1983
    Assignee: BBC, Brown, Boveri & Company, Ltd.
    Inventor: Maged A. Osman
  • Patent number: 4346244
    Abstract: Chloroalkoxybenzenes are prepared by reacting a polychlorobenzene with at least one alkali metal hydroxide and an alcohol, ROH, in the presence of at least one tertiary amine sequestering agent having the formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O).sub.n R.sub.5 ].sub.3.
    Type: Grant
    Filed: March 11, 1981
    Date of Patent: August 24, 1982
    Assignee: Rhone-Poulenc Industries
    Inventors: Gerard Soula, Louis Linguenheld
  • Patent number: 4341905
    Abstract: Hydroxyalkylphenyl ether or thioether compounds are prepared by reaction of cyclic organic carbonate compounds with phenols or thiophenols in the presence of an alkali metal halide catalyst.
    Type: Grant
    Filed: August 18, 1980
    Date of Patent: July 27, 1982
    Assignee: The Dow Chemical Company
    Inventor: Paul E. Strege
  • Patent number: 4338316
    Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.
    Type: Grant
    Filed: September 26, 1979
    Date of Patent: July 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Peter R. Marsham
  • Patent number: 4336270
    Abstract: Novel o-benzylphenols as well as a process for their production, a method for combating harmful microorganisms and compositions comprising said o-benzylphenols are provided.
    Type: Grant
    Filed: October 5, 1979
    Date of Patent: June 22, 1982
    Assignee: Ciba-Geigy Corporation
    Inventor: Rene Muntwyler
  • Patent number: 4327036
    Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.
    Type: Grant
    Filed: May 8, 1980
    Date of Patent: April 27, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank D. Marsh