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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_zacutomerck.com

M. J. Zacuto, R. F. Dunn, M. Figus, J. Org. Chem., 2014, 79, 8917-8925.

DOI: 10.1021/jo5016486 (free Supporting Information)


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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