Halogen Attached Indirectly To The Cyano Group By Nonionic Bonding Patents (Class 558/425)
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Patent number: 4824989Abstract: A (trifluoromethyl)naphthalene which has been prepared by reacting a halonaphthalene with a trifluoroacetate salt in the presence of cuprous iodide and a dipolar aprotic solvent is recovered by (1) replacing the dipolar aprotic solvent in the final reaction mixture with an alkane containing 6-12 carbons, (2) heating the resultant slurry to a temperature sufficient to dissolve the organic ingredients, (3) allowing the inorganic ingredients of the slurry to settle, (4) decanting the organic layer, and (5) cooling to precipitate the (trifluoromethyl)naphthalene.Type: GrantFiled: March 3, 1987Date of Patent: April 25, 1989Assignee: Ethyl CorporationInventor: Gary D. Heidebrecht
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Patent number: 4824988Abstract: In a process for preparing a (trifluoromethyl)napthalene by reacting a halonapthalene with a trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent and separating out the inorganic ingredients of the final reaction mixture in the recovery of the product, the cuprous iodide is recovered by washing the separated inorganic ingredients with an alcohol and a carboxylic acid and then with water to purify the cuprous iodide.Type: GrantFiled: October 26, 1987Date of Patent: April 25, 1989Assignee: Ethyl CorporationInventors: Ronny W. Lin, Venkataraman Ramachandran
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Patent number: 4820443Abstract: A cyclohexane derivative having a low viscosity, a broad nematic phase temperature range, a good compatibility with other liquid crystal components even at low temperatures and a large positive dielectric anisotropy value, and a liquid crystal composition containing the cyclohexane derivative are provided, which cyclohexane derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1-10 C and A represents a hydrogen atom, a halogen atom of F, Cl or Br or a cyano group.Type: GrantFiled: February 1, 1988Date of Patent: April 11, 1989Assignee: Chisso CorporationInventors: Yasuyuki Goto, Tetsuya Ogawa
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Patent number: 4816596Abstract: 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: GrantFiled: March 28, 1986Date of Patent: March 28, 1989Assignee: Rhone-Polenc Specialites ChimouesInventor: Bernard Langlois
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Patent number: 4814483Abstract: Optionally substituted 2-benzyl-toluenes can be prepared by reaction of optionally substituted 2-benzyl-tert.-alkyl-toluenes with an optionally substituted aromatic hydrocarbon in the presence of anhydrous iron-(III) halide. The reaction is carried out at ambient to elevated temperature. The optionally substituted aromatic hydrocarbon is employed in molar excess, relative to the 2-benzly-tert.-alkyl-toluenes.Type: GrantFiled: December 12, 1986Date of Patent: March 21, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Gunter Silber
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Patent number: 4797228Abstract: A novel cyclohexane derivative having a good stability, a low viscosity and a large dielectric aniostropy value and a liquid crystal composition containing the same are provided, which derivative is expressed by the formula ##STR1## wherein R represents an alkyl group of 1 to 10 carbon atoms; A represents hydrogen, halogen or cyano group; l represents 1 or 2; and m represents 0 or 1.Type: GrantFiled: May 28, 1986Date of Patent: January 10, 1989Assignee: Chisso CorporationInventors: Yasuyuki Goto, Shigeru Sugimori, Tetsuya Ogawa
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Patent number: 4788012Abstract: A process for the preparation of a benzyl trifluoromethyl sulfide by bringing a benzyl thiocyanate and trifluoromethyl bromide into contact with zinc in a polar aprotic solvent or a pyridine. The invention also relates to a process for the preparation of trifluoromethane sulfonyl chloride by bringing a benzyl trifluoromethyl sulfide into contact with chlorine and water.Type: GrantFiled: May 21, 1987Date of Patent: November 29, 1988Assignee: Rhone-Poulenc ChimieInventors: Catherine Francese, Marc Tordeux, Claude Wakselman
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Patent number: 4784471Abstract: The instant invention relates to compounds of the following formula: ##STR1## wherein R.sup.0 is H or linear alkyl of 1 to 7 C atoms, p is 1 or 2 and n is 0 or 2. The compounds are useful as liquid crystalline compositions in electrooptical display devices.Type: GrantFiled: October 14, 1986Date of Patent: November 15, 1988Assignee: Merck Patent Gesellschaft Mit Beschrankter HaftungInventors: Andreas Wachtler, Hans-Adolf Kurmeier, Reinhard Hittich, Bernhard Scheuble
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Patent number: 4783547Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: April 18, 1986Date of Patent: November 8, 1988Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4780559Abstract: A method for the preparation of organic fluorides which comprises reacting a quaternary phosphonium fluoride or bifluoride with an organic substrate having at least one atom or group capable of being replaced by a fluorine atom.Type: GrantFiled: January 1, 1986Date of Patent: October 25, 1988Assignee: Imperial Chemical Industries PLCInventors: Stephen J. Brown, James H. Clark
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Patent number: 4770503Abstract: Compounds of the formula ##STR1## wherein m stands for a whole number of 4-7 and n stands for 0 or a positive whole number; ring A represents trans-1,4-cyclohexylene or a 2,5-disubstituted pyrimidine ring; Z signifies a single covalent bond or, insofar as ring A represents trans-1,4-cyclohexylene, also the ethylene group --CH.sub.2 CH.sub.2 --; X denotes hydrogen or fluorine; and R represents the group --NCS or --CN,their manufacture, liquid crystalline mixtures which contain these compounds and the use of these compounds and mixtures for electro-optical purposes are described.Type: GrantFiled: May 27, 1987Date of Patent: September 13, 1988Assignee: Hoffmann-LaRoche Inc.Inventors: Richard Buchecker, Martin Schadt
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Patent number: 4751240Abstract: A phenol derivative of the formulaNU--A--X--R.sup.1wherein NU is a defined phenolic nucleus including a phenyl-hydroxynaphthyl; hydroxyphenyl-naphthyl; phenyl-hydroxyindanyl, phenyl-hydroxybenzothienyl or mono-hydroxyphenyl-ethylene or vinylene nucleus; wherein A is alkylene, alkenylene or alkynylene which may be interrupted by phenylene or other linkages, wherein R.sup.1 is hydrogen, or alkyl, alkenyl, alkynyl, cycloalkyl, halogenoalkyl, alkoxyalkyl, halogenoalkoxyalkyl, aryl or arylalkyl, or R.sup.1 is joined to R.sup.2, and wherein X is --CONR.sup.2 --, --CSNR.sup.2 --, --NR.sup.12 CO--, --NR.sup.12 CS--, --NR.sup.12 CONR.sup.2 --, ##STR1## --SO.sub.2 NR.sup.2 --or --CO--, or, when R.sup.1 is not hydrogen, is --NR.sup.12 COO--, --(PO)R.sup.2 13 , --S--, --SO--or --SO.sub.2 --, wherein R.sup.2 is hydrogen or alkyl, or R.sup.1 and R.sup.2 together form alkylene; wherein R.sup.12 is hydrogen or alkyl, and wherein R.sup.22 is hydrogen, cyano or nitro; or a salt thereof when appropriate.Type: GrantFiled: April 24, 1985Date of Patent: June 14, 1988Assignee: Imperial Chemical Industries PLCInventors: Jean Bowler, Graham C. Crawley, Philip N. Edwards, Alasdair T. Glen, Michael S. Large, Brian S. Tait
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Patent number: 4734503Abstract: Catalytic transhalogenation of haloaromatics according to the equation:C.sub.z F.sub.a X.sub.b N.sub.e L.sub.1 +C.sub.z F.sub.c X.sub.d N.sub.e L.sub.2 .fwdarw.C.sub.z F.sub.a+1 X.sub.b-1 N.sub.e L.sub.1 +C.sub.z F.sub.c-1 X.sub.d+1 N.sub.e L.sub.2wherein:when C.sub.z is a benzene derivative, a+b=5; e=0; c+d=5; z=6;when C.sub.z is a pyridine derivative, a+b=4; e=1; c+d=4; z=5;when C.sub.z is a naphthalene derivative, a+b=7; e=0; c+d=7; z=10; andwhen C.sub.z is a biphenyl derivative, a+b=9; e=0; c+d=9; z=12;L.sub.1 and L.sub.2, alike or different, are selected from F, Cl, Br, H, CN, C.sub.n F.sub.2n+1, and C.sub.6 F.sub.5 ;X is Cl, Br, or I when C.sub.z is a benzene derivative; andn is 1 to 12. This method is a novel route to known haloaromatic compounds.Type: GrantFiled: February 7, 1986Date of Patent: March 29, 1988Assignee: E. I. Du Pont De Nemours and CompanyInventor: Frank J. Weigert
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Patent number: 4734516Abstract: The reaction of a zinc compound compound of formula IIICF.sub.3 CCl.sub.2 ZnCl.yL (III)wherein y is 1 or 2 and L is a solvent ligand selected from the group consisting of the N-disubstituted acid amides, N-substituted lactams and organic sulfoxides, with an aldehyde of formula IIR--CHO (II)wherein R is an aliphatic or aromatic hydrocarbon radical or an aliphatic or aromatic heterocyclic radical, gives 1-propanols of formula I ##STR1## in high yields.Type: GrantFiled: March 19, 1986Date of Patent: March 29, 1988Assignee: Ciba-Geigy CorporationInventor: Robert W. Lang
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Patent number: 4731450Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.Type: GrantFiled: May 21, 1986Date of Patent: March 15, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Claude Wakselman, Marc Tordeux
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Patent number: 4724097Abstract: New bicyclohexylethanes of formula IR1--Cy--Cy--CH2CH2--A--(Cy)n--R2 (I)wherein R1 is alkyl; R2 is alkyl, in which one or two non-adjacent CH.sub.2 groups can be replaced by 0 atoms, or is F, Cl, Br, CN, --COOalkyl or --O--CO--alkyl; or one of the radicals R.sup.1 and R.sup.2 can also be H; A is Cy, or 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups or by a CN group; Cy is 1,4-cyclohexylene and n is 0 or 1; the alkyl groups in each case containing 1-10 C atoms, with the proviso that n is 1 if A is Cy and R2 is CN, can be used as constituents of dielectrics for electrooptical display elements.Type: GrantFiled: May 21, 1986Date of Patent: February 9, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Michael Romer, Rudolf Fidenschink, Joachim Krause, Bernhard Scheuble, Georg Weber
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Patent number: 4723005Abstract: New anisotropic compounds of the formula (1) are useful in liquid crystal mixtures for electrooptical displays; at least one of the end groups of the compounds (1) is an alkyl group which carries cyano or halogen in a terminal or non-terminal position. This offers advantages for longitudinal polarization and/or cross-polarization of the anisotropic compounds with the aid of the comparatively highly polarizing cyano or halogen substituents, in particular high clear points, low .DELTA..epsilon./.epsilon..perp. values and/or negative .DELTA..epsilon. values.Type: GrantFiled: September 10, 1984Date of Patent: February 2, 1988Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Tuong Huynh-Ba, Maged A. Osman
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Patent number: 4710315Abstract: Anisotropic compounds of the formula (1) specified in claim 1 are suitable, owing to their low .DELTA..epsilon./.epsilon..perp. values for liquid crystal displays which have high information densities of for examples up to 10.sup.6 image dots and accordingly need to be highly multiplexible; compared with known compounds they offer improved application properties and are relatively simple to synthesize.Type: GrantFiled: December 16, 1985Date of Patent: December 1, 1987Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Hans P. Schad, Stephen M. Kelly
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Patent number: 4699993Abstract: Novel compounds having greatest interest as biologically-active materials for the treatment of diabetic complications in mammals, or intermediates for such materials, are perfluoroalkyl compounds corresponding to the formula: ##STR1## wherein R and R' are independently selected from chloro, fluoro, nitro, hydroxy, and alkyl and alkoxy substituents containing 1-6 carbons; Q is --CN, --COOL, --COX, or --CTN(R")CH.sub.2 COOL; L is hydrogen, alkali metal, or saturated hydrocarbyl; X is halo; T is oxygen or sulfur; R" is an alkyl group containing 1-6 carbons; m is 0 or 1; and n is an integer of at least one.Type: GrantFiled: December 12, 1985Date of Patent: October 13, 1987Assignee: Ethyl CorporationInventor: Vernon O. Brandt
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Patent number: 4695573Abstract: There are disclosed compounds having the formula ##STR1## wherein n is 1, 2 or 3; X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, trifluoromethyl, NHCOR.sub.2 where R.sub.2 is loweralkyl, or NR.sub.3 R.sub.4 where R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R is hydrogen or loweralkyl; R.sub.1 is hydrogen, loweralkyl, diloweralkylaminoloweralkyl, arylloweralkyl, diarylloweralkyl, furylloweralkyl, thienylloweralkyl, oxygen-bridged arylloweralkyl, oxygen-bridged diarylloweralkyl, oxygen-bridged furylloweralkyl or oxygen-bridged thienylloweralkyl; Y is C.dbd.O or CR.sub.5 OH where R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 where R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR.sub.5 .dbd.CH where CR.sub.Type: GrantFiled: October 1, 1985Date of Patent: September 22, 1987Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Frank A. Pierrat
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Patent number: 4684734Abstract: Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190.degree. to 400.degree. C. under at least spontaneously generated pressure.Type: GrantFiled: September 13, 1985Date of Patent: August 4, 1987Assignee: Nippon Shokubai KK Co., Ltd.Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
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Patent number: 4680406Abstract: A novel apparatus and a process for fluorinating organic compounds from halogen-containing organic compounds is disclosed.Type: GrantFiled: October 15, 1985Date of Patent: July 14, 1987Assignee: The Dow Chemical CompanyInventor: George S. Fujioka
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Patent number: 4664840Abstract: Anisotropic compounds of the following formula: ##STR1## wherein ##STR2## is selected from the group consisting of ##STR3## Z represents a covalent bond or a carboxyl group --C(O)O--, R is selected from the group consisting of hydrogen, C.sub.1 -C.sub.12 alkyl, and C.sub.1 -C.sub.12 alkoxy and X.sup.2 and X.sup.3 may be the same or different and are selected from the group consisting of hydrogen, halogen, and nitrile, with the proviso that at least one of the groups X.sup.2 and X.sup.3 is not hydrogen, are useful as components of liquid crystal mixtures for elektrooptical twist cells.Type: GrantFiled: November 20, 1984Date of Patent: May 12, 1987Assignee: E. MerckInventor: Maged A. Osman
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Patent number: 4659502Abstract: Ethane derivatives of the formula IR.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --A.sup.2 --(A.sup.3).sub.n --R.sup.2 IwhereinR.sup.1 is H, an alkyl group with 1-12 C atoms, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms and/or CO groups and/or --O--CO-- groups and/or --CO--O groups, F, Cl, Br or R.sup.3 --A.sup.4 --Z.sup.1 --,R.sup.2 is --CN or --Z.sup.2 --A.sup.4 --CN,A.sup.1 is --A--, --A--A.sup.5 -- or --A.sup.5 --A--,A.sup.2 is an 1,4-phenylene group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms,A is a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.2 groups can also be replaced by O atoms, or is a 1,3-dithiane-2,5-diyl group or 1,4-bicyclo(2,2,2)-octylene group,A.sup.3, A.sub.4 are each a 1,4-cyclohexylene group, in which one or two non adjacent CH.sub.Type: GrantFiled: January 17, 1985Date of Patent: April 21, 1987Assignee: Merck Patent Gesellschaft mit Beschrankter HaftungInventors: Julie E. Fearon, Wendy E. Smith, George W. Gray, David Lacey, Kenneth J. Toyne, Georg Weber
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Patent number: 4631151Abstract: A fluorine-containing aromatic derivative is produced by causing a di(haloacyl)peroxide to react upon benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF.sub.2).sub.n -group into the benzene ring or the naphthalene ring.Type: GrantFiled: February 19, 1985Date of Patent: December 23, 1986Assignee: Nippon Oil & Fars Co., Ltd.Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
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Patent number: 4631286Abstract: There are disclosed compounds having the formula ##STR1## wherein X is hydrogen, loweralkyl, loweralkoxy, halogen, hydroxy, nitro, NHCOR.sub.2 wherein R.sub.2 is loweralkyl, or a group of the formula NR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R and R.sub.1 are independently hydrogen, loweralkyl, phenylloweralkyl, phenylloweralkyl in which the phenyl group is substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl, diphenylloweralkyl or diphenylloweralkyl in which one or both phenyl groups are substituted by one or more loweralkyl, loweralkoxy, halogen, hydroxy or trifluoromethyl; Y is C.dbd.O or CR.sub.5 OH wherein R.sub.5 is hydrogen or loweralkyl; Z is CH.sub.2 or C.dbd.CR.sub.6 R.sub.7 wherein R.sub.6 and R.sub.7 are independently hydrogen or loweralkyl; or Y and Z taken together is CR.sub.5 .dbd.CH wherein CR.sub.Type: GrantFiled: October 25, 1984Date of Patent: December 23, 1986Assignee: Hoechst-Roussel Pharmaceuticals Inc.Inventors: Gregory M. Shutske, Frank A. Pierrat
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Patent number: 4590315Abstract: A process for the preparation of chloro-difluorobenzene compounds of the formula ##STR1## where R is CN or CF.sub.3, comprises the steps of (A) reacting an alkali metal fluoride with 4-chloro-3,5-dinitrobenzonitrile or 4-chloro-3,5-dinitrobenzotrifluoride to form the corresponding 4-fluoro-3,5-dinitrobenzonitrile or 4-fluoro-3,5-dinitrobenzotrifluoride product.(B) chlorodenitrating the 4-fluoro product of step (A) to form the corresponding 3,5-dichloro-4-fluorobenzonitrile or 3,5-dichloro-4-fluorobenzotrifluoride compound.(C) reacting the 3,5-dichloro-4-fluorobenzonitrile or 3,5-dichloro-4-fluorobenzotrifluoride compound prepared in step (B) with an alkali metal fluoride to form the corresponding 3-chloro-4,5-difluorobenzonitrile or 3-chloro-4,5-difluorobenzotrifluoride compound.Type: GrantFiled: October 15, 1984Date of Patent: May 20, 1986Assignee: Occidental Chemical CorporationInventors: James J. Maul, David Y. Tang
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Patent number: 4582948Abstract: 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: GrantFiled: April 27, 1984Date of Patent: April 15, 1986Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
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Patent number: 4575571Abstract: 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: GrantFiled: June 22, 1984Date of Patent: March 11, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel Desbois, Camille Disdier