Nucleophilic substitution process

Details Nucleophilic substitution process Nucleophilic substitution process

1981-11-02

1983-01-25

Torrence, Dolph H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465G, 562492, C07C12178, C07C12166, C07C 53132

Patent

active

043702783

ABSTRACT:
2-(Fluoronitrobenzene)alkyl cyanides are prepared by reacting a fluoronitrobenzene with an alpha-substituted alkyl cyanide in a substantially anhydrous aprotic solvent and in the presence of a base so that the alkyl cyanide reactant undergoes a nucleophilic substitution reaction on an unsubstituted carbon atom of the fluoronitrobenzene during which the alpha-substituent of the alkyl cyanide reactant functions as a leaving group. Use of 2-fluoronitrobenzene and an alpha-substituted propionitrile (e.g., 2-chloropropionitrile) produces a novel compound, 2-(3-fluoro-4-nitrobenzene)propionitrile. Reduction of the nitro substituent produces another novel compound, 2-(4-amino-3-fluorobenzene)proprionitrile. This can readily be converted to 2-(3-fluoro-4-biphenylyl)propionitrile by means of a Gomberg-Bachmann reaction with an aromatic hydrocarbon or substituted aromatic hydrocarbon which in turn can be converted on hydrolysis into the corresponding 2-(2-fluoro-4-biphenylyl)propionic acid. Use of benzene in the Gomberg-Bachmann reaction thus enables production of flurbiprofen, a well-known pharmaceutical.

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patent: 4278516 (1981-07-01), Zaiko et al.
Golinski et al., Tetrahedron Letters, 37, pp. 3495-3498, (1978).
Makosza et al., J. Org. Chem., 45, 1534-1535, (1980).
Miyamatsu et al., J. of Medicinal Chem., vol. 17, 491-496, (1974).
Sunwell et al., J. of Medicinal Chem., vol. 18, 692-694, (1975).

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