Reaction of Phenols with t-Butyl Bromide-Dimethyl Sulphoxide. Methylthiomethylation versus Bromination

Article abstract of DOI:10.1039/P19830001141

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.