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Simple, Rapid Procedure for the Synthesis of Chloromethyl Methyl Ether and Other Chloro Alkyl Ethers¹

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Martin A. Berliner* and Katherine Belecki

Chemical Research and Development, Pfizer Global Research and Development, Groton Labs, Groton, Connecticut 06340 martin.a.berliner@pfizer.com

J. Org. Chem., 2005, 70 (23), pp 9618–9621

DOI: 10.1021/jo051344g

Publication Date (Web): October 13, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Zinc(II) salts catalyze the reaction between acetals and acid halides to provide haloalkyl ethers in near-quantitative yield. Reactions from millimole to mole scale are typically complete in 1−4 h with 0.01 mol % catalyst. The solutions of haloalkyl ethers thus obtained can be utilized directly in reactions in which the presence of the ester byproduct does not interfere. Excess haloalkyl ether is destroyed on workup, thereby minimizing exposure to this class of carcinogenic compounds.

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Published In Issue November 11, 2005
Received June 29, 2005

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Simple, Rapid Procedure for the Synthesis of Chloromethyl Methyl Ether and Other Chloro Alkyl Ethers¹