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

doi:10.1055/s-2004-831230

SHORTPAPER

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;

Abstract

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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.

Key words

sulfones - halogenation - alkynes - allenes - thiols

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Referenzen

References

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