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US 4,144,397 AGranted
Preparation of 2-aryl-propionic acids by direct coupling utilizing a mixed magnesium halide complex
AssigneeSyntex Corporation
InventorsGary J. Matthews, Robert A. Arnold
Life of this patent
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Abstract
Valuable 2-aryl-propionic acids are prepared by the direct coupling of aryl magnesium bromides with a mixed magnesium halide complex of alpha-bromopropionic acid.
Claims11
A process for the preparation of a 2-arylpropionic acid wherein aryl is selected from the group consisting of 6-methoxy-2-naphthyl, 4-alkylphenyl and 4'-fluoro-4-biphenyl which process comprises:
- (a) contacting a solution of an aryl magnesium bromide with a solution of a complex, CH.sub.3 CH(Br)COOMgX, wherein X is chloro or bromo, in an aprotic organic solvent medium comprising an ether, and
- (b) quenching the reaction mixture from (a) with acid.
A process for the preparation of 2-(6-methoxy-2-naphthyl)propionic acid which process comprises:
- (a) contacting an approximately 0.5 to 2.0 molar solution of 2-(6-methoxynaphthyl)magnesium bromide in tetrahydrofuran with an approximately 1.0 to 2.0 molar solution of alpha-bromopropionic acid mixed magnesium chloride or bromide complex in tetrahydrofuran, at a temperature between about 0.degree. and 100.degree. C., and
- (b) quenching the reaction mixture from step (a) with acid.
Dependencies are inferred from the claim text.