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Synthesis 2009(2): 306-310  
DOI: 10.1055/s-0028-1083273
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Molybdenum(VI) Dichloride Dioxide Catalyzed Conversion of β-Hydroxy­carbonyls into α-Bromo 1,3-Dicarbonyls by N-Bromosuccinimide

Kandasamy Jeyakumar, Dillip Kumar Chand*
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India
Fax: +91(44)22574202; e-Mail: dillip@iitm.ac.in;
Further Information

Publication History

Received 2 September 2008
Publication Date:
12 December 2008 (online)

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Abstract

A novel and efficient method for the one-pot transformation of β-hydroxycarbonyl compounds to α-brominated 1,3-dicarbonyl compounds is achieved with MoO2Cl2 in the presence of N-bromosuccinimide. All the reactions were carried out under mild conditions and provide good yields of the products. No bromination occurs at benzylic and allylic positions.

Key words

β-hydroxycarbonyl compounds - oxidation - bromination - molybdenum - N-bromosuccinimide

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