发明名称 |
Nucleophilic substitution process |
摘要 |
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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申请公布号 |
US4370278(A) |
申请公布日期 |
1983.01.25 |
申请号 |
US19810317321 |
申请日期 |
1981.11.02 |
申请人 |
ETHYL CORPORATION |
发明人 |
STAHLY, BARBARA C.;STAHLY, G. P. |
分类号 |
C07D209/46;C07C53/132;C07C67/00;C07C201/00;C07C205/56;C07C227/00;C07C227/02;C07C227/04;C07C229/42;C07C253/00;C07C255/32;C07C255/35;C07C255/42;C07D207/333;C07D209/48;(IPC1-7):C07C121/78;C07C121/66;C07C53/13 |
主分类号 |
C07D209/46 |
代理机构 |
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代理人 |
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主权项 |
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地址 |
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