Cg. Ferrayoli et al., ALTERNATIVE SYNTHESIS OF 2-ARYLPROPANOIC ACIDS FROM ENOLATE AND ARYL HALIDES, Journal of the Chemical Society. Perkin transactions. I, (12), 1995, pp. 1635-1638
Arylpropanoic acids, a type of non-steroidal antiinflammatory drug, ha
ve been prepared in liquid ammonia by photo-radical nucleophilic subst
itution of halogenoarenes with sodium N,N-dimethylacetamide enolate fo
llowed by methylation and hydrolysis. Rapid substitution occurred in m
any cases with good to excellent yields of arylpropanoic acids. The ti
tle compounds have also been prepared by arylation of sodium acetone e
nolate with methylation and oxidation in a haloform reaction.