Table of Contents
ISRN Organic Chemistry
Volume 2014 (2014), Article ID 751298, 11 pages
http://dx.doi.org/10.1155/2014/751298
Research Article

Substrate Directed Regioselective Monobromination of Aralkyl Ketones Using N-Bromosuccinimide Catalysed by Active Aluminium Oxide: α-Bromination versus Ring Bromination

Department of Chemistry, School of Physical Sciences, Yogi Vemana University, Kadapa, Andhra Pradesh 516 003, India

Received 23 November 2013; Accepted 24 December 2013; Published 4 March 2014

Academic Editors: M. D'Auria, M. Parra, J. Wu, and N. Zanatta

Copyright © 2014 Reddy Bodireddy Mohan et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Bromination of aralkyl ketones using N-bromosuccinimide in presence of active Al2O3 provided either α-monobrominated products in methanol at reflux or mononuclear brominated products in acetonitrile at reflux temperature with excellent isolated yields depending on the nature of substrate employed. The α-bromination was an exclusive process when aralkyl ketones containing moderate activating/deactivating groups were subjected to bromination under acidic Al2O3 conditions in methanol at reflux while nuclear functionalization was predominant when aralkyl ketones containing high activating groups were utilized for bromination in presence of neutral Al2O3 conditions in acetonitrile at reflux temperature. In addition, easy isolation of products, use of inexpensive catalyst, short reaction time (10–20 min), and safe operational practice are the major benefits in the present protocol.