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

Mameda Naresh; Macharla Arun Kumar; Marri Mahender Reddy; Peraka Swamy; Jagadeesh Babu Nanubolu; Nama Narender

doi:10.1055/s-0033-1338431

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(11): 1497-1504
DOI: 10.1055/s-0033-1338431

paper

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

Autor*innen

Mameda Naresh

^aI&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in
Macharla Arun Kumar

^aI&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in
Marri Mahender Reddy

^aI&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in
Peraka Swamy

^aI&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in
Jagadeesh Babu Nanubolu

^bX-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
Nama Narender*

^aI&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India Fax: +91(40)27160387 eMail: narendern33@yahoo.co.in

Abstract

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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.

Key words

halogenation - bromination - arenes - regioselectivity - aryl halides

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Referenzen

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