Chemo- and regioselective demethylation of 2-bromo-α-resorcylic acid derivatives using alkylthiolate salts

Abstract

We report here the chemo- and regioselective demethylation of 3,5-dimethoxy-2-bromo-α-resorcylic acid esters by a thiolate nucleophilic displacement reaction. Optimized conditions facilitate yields up to 93% for o-bromo selective demethylation of diverse ester derivatives of dimethoxy 2-bromo-α-resorcylic acid. Our results highlight a new, efficient, and reliable demethylation reagent, as well as a useful steric bias directing strategy.