A Mild and Regioselective Method for α-Bromination of β-Keto Esters and 1,3-Diketones Using Bromodimethylsulfonium Bromide (BDMS)

Abu T. Khan,* Md Ashif Ali, Papori Goswami, and Lokman H. Choudhury
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781 039, India atk@iitg.ernet.in
J. Org. Chem., 2006, 71 (23), pp 8961–8963
DOI: 10.1021/jo061501r
Publication Date (Web): October 11, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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Bromodimethylsulfonium bromide has been found to be an effective and regioselective reagent for α-monobromination of β-keto esters and 1,3-diketones. A wide variety of β-keto esters and 1,3-diketones undergo chemoselective α-monobromination with excellent yields at 0−5 °C or room temperature. The notable advantages of this protocol are no need of chromatographic separation, use of less hazardous reagent than molecular bromine, and no added base, Lewis acid, or other catalyst.

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  • Published In Issue November 10, 2006
  • Received July 19, 2006

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