Mild Regioselective Monobromination of Activated Aromatics and Heteroaromatics with<i>N</i>-Bromosuccinimide in Tetrabutylammonium Bromide

Abstract

Highly regioselective nuclear bromination of activated aromatic and heteroaromatic compounds has been accomplished using N-bromosuccinimide in tetrabutylammonium bromide. Predominant para-selective monobromination of activated aromatics such as phenols and anilines, rate acceleration of bromination for moderately activated and less reactive substrates on addition of acidic montmorillonite K-10 clay, with or without microwave assistance, are the notable features of this protocol.