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Tetrahedron Letters

Tetrahedron Letters

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Non-phosgene synthesis of benzyl chloroformate (CbzCl)

Published:21 October 2002 DOI: 10.1016/S0040-4039(02)01834-8
Takumi Mizuno , Junko Takahashi , Akiya Ogawa

Abstract

A novel synthetic method for benzyl chloroformate (CbzCl) using carbon monoxide or carbonyl sulfide as a carbonyl source was established. Benzyl chloroformate was successfully synthesized by the chlorination using sulfuryl chloride of S-methyl O-benzyl carbonothioate, which was prepared by the carbonylation of benzyl alcohol with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) followed by esterification using methyl iodide.

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