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United States Patent (19) 11) 4,370,278 Stahly Et Al

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United States Patent (19) 11) 4,370,278 Stahly Et Al United States Patent (19) 11) 4,370,278 Stahly et al. 45) Jan. 25, 1983 54) NUCLEOPHILIC SUBSTITUTION PROCESS Sunwell et al., J. of Medicinal Chem., vol. 18, 692-694, 75) Inventors: Barbara C. Stahly; G. P. Stahly, both (1975). of Baton Rouge, La. Primary Examiner-Dolph H. Torrence 73 Assignee: Ethyl Corporation, Richmond, Va. Attorney, Agent, or Firm-Donald L. Johnson; John F. (21) Appl. No.: 317,321 Sieberth 57 ABSTRACT 22 Filed: Nov. 2, 1981 2-(Fluoronitrobenzene)alkyl cyanides are prepared by 51) Int. Cl. .................. C07C 121/78; CO7C 121/66; reacting a fluoronitrobenzene with an alpha-substituted CO7C 53/132 alkyl cyanide in a substantially anhydrous aprotic sol 52 U.S. Cl. ........................... 260/465 E; 260/465 G; vent. and in the presence of a base so that the alkyl 562/492 cyanide reactant undergoes a nucleophilic substitution 58) Field of Search ....................... 260/46.5 G, 465 E; reaction on an unsubstituted carbon atom of the 562/492 fluoronitrobenzene during which the alpha-substituent 56) References Cited of the alkyl cyanide reactant functions as a leaving group. Use of 2-fluoronitrobenzene and an alpha-sub U.S. PATENT DOCUMENTS stituted propionitrile (e.g., 2-chloropropionitrile) pro 3,755,427 8/1973 Adams et al. ....................... 562/492 duces a novel compound, 2-(3-fluoro-4-nitrobenzene)- 3,920,839 11/1975 Wasley ............. ... 424/319 propionitrile. Reduction of the nitro substituent pro 3,959,364 5/1976 Armitage et al. ... 562/492 duces another novel compound, 2-(4-amino-3- 4,278,516 7/1981 Zaiko et al. ......... ... 204/158 HA fluorobenzene)proprionitrile. This can readily be con verted to 2-(3-fluoro-4-biphenylyl)propionitrile by FOREIGN PATENT DOCUMENTS means of a Gomberg-Bachmann reaction with an aro 45-28369 9/1970 Japan. matic hydrocarbon or substituted aromatic hydrocar bon which in turn can be converted on hydrolysis into OTHER PUBLICATIONS the corresponding 2-(2-fluoro-4-biphenylyl)propionic Golinski et al., Tetrahedron Letters, 37, pp. 3495-3498, acid. Use of benzene in the Gomberg-Bachmann reac (1978). tion thus enables production of flurbiprofen, a well Makosza et al., J. Org. Chem, 45, 1534-1535, (1980). known pharmaceutical. Miyamatsu et al., J. of Medicinal Chem., vol. 17, 491-496, (1974). 20 Claims, No Drawings 4,370,278 1 2 group, preferably by means of a Gomberg-Bachmann NUCLEOPHILIC SUBSTITUTION PROCESS reaction. A further embodiment involves converting the resul TECHNICAL FIELD tant 2-(fluorobiphenylyl)alkyl cyanides into the corre This invention relates to a process for the preparation 5 sponding '-(fluorobiphenylyl) alkanoic acids. of 2-(fluoronitrobenzene)alkylcyanides, also known as Thus in a particularly preferred embodiment flurbi 2-(fluoronitrobenzene) carboxylic acid nitriles. More profen is produced by (i) reacting 2-fluoronitrobenzene particularly this invention relates to the production of with an alpha-substituted propionitrile in a substantially 2-(3-fluoro-4-nitrobenzene)propionitrile and 2-(4- anhydrous aprotic solvent and in the presence of a base amino-3-fluorobenzene)propionitrile, novel compounds 10 so that the alpha-substituted propionitrile undergoes a which are especially useful in the production of flurbi nucleophilic substitution reaction on the unsubstituted profen by a new economical synthesis process, carbon atom of the fluoronitrobenzene para to the nitro group during which the alpha-substituent of the propio BACKGROUND nitrile functions as a leaving group and 2-(3-fluoro-4- The compound 2-(2-fluoro-4-biphenylyl)propionic 15 nitrobenzene)propionitrile is formed, (ii) reducing the acid-known as flurbiprofen-is a well known drug nitro substituent of said 2-(3-fluoro-4-nitrobenzene)pro which possesses desirable anti-inflammatory, analgesic pionitrile to an amino substituent so that 2-(4-amino-3- and anti-pyretic properties. Flurbiprofen and methods fluorobenzene)propionitrile is formed, (iii) converting for its preparation are disclosed in U.S. Pat. Nos. said 2-(4-amino-3-fluorobenzene)propionitrile into 2-(2- 3,755,427 and 3,959,364. The former discloses a method 20 fluoro-4-biphenylyl)propionitrile preferably by means for its preparation by reacting an ester of the appropri of a Gomberg-Bachmann reaction with benzene, and ate substituted 4-biphenylyl acetic acid with diethyl (iv) converting said. 2-(2-fluoro-4-biphenylyl)propioni carbonate to give a malonic ester, methylating the so trile into 2-(2-fluoro-4-biphenylyl)propionic acid. dium derivative of this di-ester, hydrolyzing the di A variety of fluoronitrobenzenes can be used in the ester, and then decarboxylating the resulting di-acid. 25 practice of this invention and thus use may be made of The latter patent discloses a process for the preparation such compounds as 3-fluoronitrobenzene, 4-fluoroni of aryl propionic acids-including flurbiprofen-13 by trobezene; 2,3-difluoronitrobenzene; 2,4-difluoronitro reacting a Grignard compound, obtained from an aryl benzene; 2,5-difluoronitrobenzene; 2,6-difluoronitro bromide and magnesium, with a lithium, sodium, mag 30 benzene; 3,4-difluoronitrobenzene; 3,5-difluoronitro nesium or calcium salt of 2-bromopropionic acid, fol benzene as well as the various trifluoronitrobenzenes lowed by acidification. U.S. Pat. No. 4,278,516 discloses and tetrafluoronitrobenzenes preferably having an un an improved synthesis process in which flurbiprofen substituted ortho or para position. Most preferably the can be prepared in a sequence of steps starting with para position relative to the nitro group of the fluoroni 2-amino-4-methylbiphenyl. 35 trobenzene reactant is unsubstituted as the nucleophilic substitution reaction of this invention tends to be highly THE INVENTION selective on the para position and thereby produces A new process for the synthesis of flurbiprofen and 2-(fluoronitrobenzene)alkyl cyanides which are ideally related fluorobiphenylyl alkanoic acid derivatives has suited for the synthesis of flurbiprofen and related now been discovered in which these materials can be 40 fluorobiphenylyl alkanoic acid derivatives. A particu prepared in a simple and straightforward manner with larly preferred reactant is 2-fluoronitrobenzene which out need for tedious and time-consuming operations can be readily converted in good yield with high selec associated with conventional processes. In this new tivity into flurbiprofen itself via the four-step reaction process 2-(fluoronitrobenzene)alkyl cyanides are pro sequence described above. , duced in a novel synthesis reaction and used as interme 45 Likewise, a variety of alpha-substituted alkyl cya diates in a reaction sequence in which, inter alia, 2 nides may be used in practicing this invention. In gen (aminofluorobenzene)alkyl cyanides are likewise pro eral these alkylcyanides which contain a leaving group, duced and used as reaction intermediates. L, in the alpha-position may be represented by the for This invention thus involves in one embodiment the mula: discovery that 2-(fluoronitrobenzene)alkyl cyanides can 50 be readily prepared in good yield with high selectivity L by reacting a fluoronitrobenzene with an alpha-sub N stituted alkyl cyanide in a substantially anhydrous CHCN / aprotic solvent and in the presence of a base so that the R alkyl cyanide reactant undergoes a nucleophilic substi 55. tution reaction on an unsubstituted carbon atom of the wherein R is hydrogen; a hydrocarbyl group (e.g., al fluoronitrobenzene during which the alpha-substituent kyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, of the alkyl cyanide reactant functions as a leaving aralkyl, etc.) preferably containing up to about 10 car group. bon atoms; halogen, preferably bromine and most pref In another embodiment of this invention 2-(amino 60 erably chlorine; or a hydrocarbyloxyalkyl group. Ex fluorobenzene)alkyl cyanides are produced by forming emplary leaving groups, L, include the following: alk a 2-(fluoronitrobenzene)alkyl cyanide in the above man oxy, cycloalkoxy, aryloxy, aralkoxy, haloalkoxy, ner and then reducing the nitro substituent of the 2 halocycloalkoxy, haloaryloxy, haloaralkoxy, alkylthio, (fluoronitrobenzene)alkylcyanide to an amino substitu cycloalkylthio, arylthio, aralkylthio, haloalkylthio, ent. 65 halocycloalkylthio, haloarylthio, haloaralkylthio, and In still another embodiment 2-(fluorobiphenylyl)alkyl the like. Other suitable leaving groups have been re cyanides are formed by replacing the amino group of ferred to in the literature-see for example Tetrahedron the 2-(aminofluorobenzene)alkyl cyanides by an aryl Letters 37,3495-8 (1978) and J. Org. Chem. 45, 1534-5 4,370,278 3 4. (1980). Since the leaving group does not remain in the ide, sodium hydroxide, potassium hydroxide, etc.). If resultant product it is preferable to employ an alkyl desired a phase transfer catalyst such as a quaternary cyanide in which this alpha-substituent contains no ammonium halide or a suitable crown ether may be used more than about 10 carbon atoms although organic along with the alkali metal hydroxide. In this instance leaving groups having an even higher carbon content the reaction medium preferably includes or consists of are deemed satisfactory. Preferred leaving groups are an inert liquid hydrocarbon such as hexane, heptane, the halogens, viz., fluorine or iodine, preferably bro isooctane, ligroin, toluene, xylene, or the like. When mine and most preferably chlorine. Thus in accordance employing crown ethers in such phase transfer catalytic with one preferred embodiment of this invention the systems
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