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Issue 2, 2008
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An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives and ketones using a bromide/bromate couple

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Abstract

Mixtures of NaBr and NaBrO3 in two different ratios have been used for highly stereoselective bromination of alkenes and alkynes, and regioselective bromine substitution at the α-carbon of ketones and at the benzylic position of toluene derivatives. The reactions were conducted in an aqueous acidic medium under ambient conditions. The solid reagents were prepared from the intermediate obtained in the “cold process” of bromine manufacture and are stable, non-hazardous and inexpensive to prepare. This procedure provides an efficient and practical alternative to conventional procedures using liquid bromine directly or indirectly.

Graphical abstract: An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives and ketones using a bromide/bromate couple

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Publication details

The article was received on 10 Sep 2007, accepted on 16 Nov 2007 and first published on 03 Dec 2007


Article type: Paper
DOI: 10.1039/B713829F
Green Chem., 2008,10, 232-237

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    An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives and ketones using a bromide/bromate couple

    S. Adimurthy, S. Ghosh, P. U. Patoliya, G. Ramachandraiah, M. Agrawal, M. R. Gandhi, S. C. Upadhyay, P. K. Ghosh and B. C. Ranu, Green Chem., 2008, 10, 232
    DOI: 10.1039/B713829F

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