Microwave-Assisted NBS Bromination of p-Iminotoluenes: Preparation of New Alcohol, Mercapto, and Amino Protection Groups

Abstract

A simple, efficient, safe, high-yielding and rapid microwave-assisted method for the preparation of protected p-bromomethyl and p-dibromomethylanilines was developed as new alcohol, thiol, and amine protection groups. The procedure involves microwave-assisted N-bromosuccinimide (NBS) radical bromination of readily available N-protected p-toluidine. The microwave-assisted radical bromination was found to be superior to the conventional NBS radical bromination.

Keywords:

• Benzyl bromides
• microwave-assisted reactions
• NBS bromination
• radical bromination

ACKNOWLEDGMENT

We thank the National Science Foundation for financial support (CHE-0611902) for this work.