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Article

A Simple and Efficient Method for Regioselective and Stereoselective Synthesis of Vicinal Bromohydrins and Alkoxybromides from an Olefin

Supporting Info

Prodeep Phukan,* Pranita Chakraborty, and Dolly Kataki

Department of Chemistry, Gauhati University, Guwahati 781014, Assam, India

J. Org. Chem., 2006, 71 (20), pp 7533–7537

DOI: 10.1021/jo0600611

Publication Date (Web): September 7, 2006

To whom correspondence should be addressed. Tel: +91-361-2570535 (O). Fax: +91-361-2700311.

, pphukan@yahoo.com

Abstract

A very rapid and efficient method has been developed for the synthesis of vicinal bromohydrins and alkoxybromides directly from an olefin without any catalyst. The reaction was performed in CH₃CN−water (4:1) or alcohol using N,N-dibromo-p-toluenesulfonamide (TsNBr₂) as the brominating agent. Excellent yields and regio- and stereoselectivities have been obtained. Bromohydrins are formed instantaneously, whereas formation of alkoxybromides takes 30−60 min.

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