A mild, convenient, and inexpensive procedure for conversion of vinyl halides to α-haloketones

MP VanBrunt, RO Ambenge…

Index: VanBrunt, Michael P.; Ambenge, Reuben O.; Weinreb, Steven M. Journal of Organic Chemistry, 2003 , vol. 68, # 8 p. 3323 - 3326

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Citation Number: 41

Abstract

Treatment of a vinyl chloride with commercially available aqueous sodium hypochlorite solution in a 2: 5 mixture of acetic acid/acetone at 0° C for about 1 h cleanly leads to the corresponding α-chloroketone. Similarly, if a vinyl bromide is exposed to sodium hypobromite (freshly prepared from bromine and sodium hydroxide) at 0° C in 2: 5 acetic acid/acetone as solvent, an α-bromoketone is produced. This methodology has been ...