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Synlett 2006(10): 1619-1620  
DOI: 10.1055/s-2006-941579
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Bromodimethylsulfonium Bromide (BDMS): A Versatile Reagent in Organic Synthesis

Md Lokman Hakim Choudhury*
Department of Chemistry, Indian Institute of Technology ­Guwahati, Guwahati 781 039, India
e-Mail: mlhc@iitg.ernet.in; e-Mail: lokman_iitg@yahoo.com;
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Publication History

Publication Date:
12 June 2006 (online)

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Introduction

Bromodimethylsulfonium bromide (BDMS) (Figure 1) is a light orange solid compound, which has been used extensively in various organic transformations. It can easily be prepared from molecular bromine and dimethyl­sulfide. [1] It can also be generated in situ from the reaction of dimethylsulfoxide and aqueous HBr. [2] BDMS can be considered a convenient storage for the bromonium ion, just as hypobromite, N-bromosuccinimide or bromoazide. After Meerwein’s discovery of bromodimethylsulfonium bromide in 1965, [3] it has gained considerable interest in current organic chemistry due to its easy handling and low cost, its easy access and varied application both as ­catalyst, [4-10] as well as an effective reagent.

Figure 1 Bromodimethylsulfonium bromide (BDMS)