Preparation of α-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation
Wei Li,* Jianchang Li, Zhao-Kui Wan, Junjun Wu and Walter Massefski
*Chemical and Screening Sciences, Wyeth Research, 200
Cambridge Park Drive, Cambridge, Massachusetts 02140, Email: weili
wyeth.com
W. Li, J. Li, Z.-K. Wan, J. Wu, W. Massefski, Org. Lett., 2007, 9, 4607-4610.
DOI: 10.1021/ol7021142
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Abstract
α,β-Dihalopropanoate derivatives undergo efficient, selective dehydrohalogenation to form α-haloacrylate analogues in the presence of DMSO. A variety of α-halo Michael acceptors were prepared in dimethyl sulfoxide under mild, base-free conditions, including the preparation of α-bromoacrolein and α-chloro- and bromoacrylonitriles.
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W. Li, J. Li, M. Lin, S. Wacharasindhu, K. Tabei, T. S. Mansour, J. Org. Chem., 2007, 72, 6016-6021.
Key Words
unsaturated compounds, vinyl bromides
ID: J54-Y2007-3470
