Halogenation with Copper(II). I. Saturated Ketones and Phenol

Edward M. Kosower*, W. J. Cole, G. S. Wu, D. E. Cardy, G. Meisters

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


A procedure for halogenation of enolizable compounds using copper(II) chloride or bromide in dimethylformamide is described. Methyl ethyl ketone yields 55–70% 3-chlorobutanone, methyl cyclopropyl ketone yields both chloromethyl and dichloromethyl cyclopropyl ketones, propiophenone gives an excellent yield of α-chloropropiophenone, and phenol leads to o- and p-chlorophenols, in a ratio (1:6) substantially different from that of other chlorination methods, along with some 2,4-dichlorophenol. A convenient test for relative reactivities of enols and enolizable compounds is also included.

Original languageEnglish
Pages (from-to)630-633
Number of pages4
JournalJournal of Organic Chemistry
Issue number3
StatePublished - 1 Mar 1963
Externally publishedYes


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