Synthesis of Ethyl Arylacetates by Means of Friedel-Crafts Reaction of Aromatic Compounds with Ethyl α-Chloro-α-(methylthio) acetate

Abstract

Friedel-Crafts reaction of aromatic compounds with ethyl α-chloro-α-(methylthio)-acetate (1) gave ethyl α-(methylthio) arylacetates (2), which were readily converted into ethyl arylacetates (3) by reductive desulfurization with Raney nickel or zinc dust-acetic acid. The reactions were applied to the syntheses of ibufenac (5) and alclofenac (6), which are anti-inflammatory agents.