Bromination of cumene and some 4-hydroxycumenes with N-bromosuccinimide

Abstract

Bromination of cumene with N-bromosuccinimide yielded 1,2-dibromo-2-phenylpropane, whereas 4-hydroxycumene gave either 3-bromo-4-hydroxycumene, 3,5-dibromo-4-hydroxycumene, or 1,3-dibromo-2-(3,5-dibromo-4-hydroxyphenyl)propene depending on the excess of reagent used. Similarly 4-hydroxy-3,5-di-t-butylcumene gave either 1,3-dibromo-2-(4-hydroxy-3,5-di-t-butylphenyl)propene or 1,3-dibromo-2-(2-bromo-4-oxo-3,5-di-t-butylcyclohexa-2,5-dienyl)propene.