A Mild, Convenient, and Inexpensive Procedure for Conversion of Vinyl Halides to α-Haloketones
- 21 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (8), 3323-3326
- https://doi.org/10.1021/jo020739m
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 applied to a number of vinyl chlorides and vinyl bromides, and the transformations generally proceed in high yields. The mild reaction conditions are compatible with a variety of functional groups including amides, esters, and imines.This publication has 7 references indexed in Scilit:
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