One-Step Synthesis of 1-Chloro-3-arylacetone Derivatives from Arylacetic Acids
Michael J. Zacuto*, Robert F. Dunn and Margaret Figus
*Department of Process Research, Merck Research Laboratory,
Rahway, New Jersey 07065, United States, Email: michael_zacuto
merck.com
M. J. Zacuto, R. F. Dunn, M. Figus, J. Org. Chem., 2014, 79, 8917-8925.
DOI: 10.1021/jo5016486
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Abstract
A practical one-step method for the preparation of α-chloroketones from readily available, inexpensive phenylacetic acid derivatives utilizes the unique reactivity of an intermediate Mg-enolate dianion, which displays selectivity for the carbonyl carbon of chloromethyl carbonyl electrophiles. Decarboxylation of the intermediate occurs spontaneously during the reaction quench.
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Key Words
Weinreb ketone synthesis, decarboxylation, α-chloroketones
ID: J42-Y2014
