Synthesis 2004(16): 2611-2613  
DOI: 10.1055/s-2004-831230
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Improved Synthesis of 2,3-Dibromo-1-(phenylsulfonyl)-1-propene (DBP)

Aaron VanZanten, Katherine Mullaugh, Ryan Harrington, Adam Kiefer, David Carlson, Dan Mastarone, Corey Lipchik, S. Shaun Murphree*
Department of Chemistry, Allegheny College, Meadville, PA 16335, USA
Fax: +1(814)3322789; e-Mail: smurphre@allegheny.edu;
Further Information

Publication History

Received 6 May 2004
Publication Date:
22 September 2004 (online)

Abstract

A convenient preparation of 2,3-dibromo-1-(phenylsulfonyl)-1-propene (DBP, 1) is available through the one-pot propargylation and oxidation of thiophenol to give the propargyl sulfone 11, which is isomerized and brominated in another one-pot reaction. The new preparation is significantly more scalable, as well as more convenient and robust than the prior art.