Synthesis 2013; 45(11): 1497-1504
DOI: 10.1055/s-0033-1338431
paper
© Georg Thieme Verlag Stuttgart · New York

Fast and Efficient Bromination of Aromatic Compounds with Ammonium Bromide and Oxone

Mameda Naresh
a   I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: narendern33@yahoo.co.in
,
Macharla Arun Kumar
a   I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: narendern33@yahoo.co.in
,
Marri Mahender Reddy
a   I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: narendern33@yahoo.co.in
,
Peraka Swamy
a   I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: narendern33@yahoo.co.in
,
Jagadeesh Babu Nanubolu
b   X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
,
Nama Narender*
a   I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India   Fax: +91(40)27160387   Email: narendern33@yahoo.co.in
› Author Affiliations
Further Information

Publication History

Received: 05 February 2013

Accepted after revision: 28 March 2013

Publication Date:
14 May 2013 (online)


Abstract

A highly efficient, rapid and regioselective protocol was developed for the ring bromination of aromatic compounds under mild conditions with ammonium bromide as a source of bromine source and Oxone® (potassium peroxysulfate) as an oxidant. No metal catalyst or acidic additive is required. A variety of aromatic compounds, including methoxy, hydroxy, amino, and alkyl arenes, reacted smoothly to give the corresponding monobrominated products in good to excellent yields in very short reaction times. Moreover, dibromination of deactivated anilines to give the corresponding dibromides proceeded in high yields. Interestingly, 1-(2-naphthyl)ethanone provided a ring-brominated product.

Supporting Information