Alternative synthesis of 2-arylpropanoic acids from enolate and aryl halides

Abstract

Arylpropanoic acids, a type of non-steroidal antiinflammatory drug, have been prepared in liquid ammonia by photo-radical nucleophilic substitution of halogenoarenes with sodium N,N-dimethylacetamide enolate followed by methylation and hydrolysis. Rapid substitution occurred in many cases with good to excellent yields of arylpropanoic acids. The title compounds have also been prepared by arylation of sodium acetone enolate with methylation and oxidation in a haloform reaction.