Reaction of phenols with t-butyl bromide–dimethyl sulphoxide. Methylthiomethylation versus bromination

Abstract

t-Butyl bromide-activated dimethyl sulphoxide reacts with phenols to give either methylthiomethylation or bromination products. Several equilibria are shown to be simultaneously present in the system; however, by appropriate choice of several parameters (basicity, temperature, and reactant ratio) it is possible to drive the reaction selectively in one direction. A general discussion on the mechanism of these reactions is given.