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Short Paper | Regular issue | Vol 92, No. 12, 2016, pp.2261-2270
Published online, 4th November, 2016
DOI: 10.3987/COM-16-13579
Synthesis of 1-Aryl-1,3-dihydrobenzo[c]thiophenes by Acid-Mediated Cyclization of 1-[Aryl(methoxy)methyl]-2-[(tert-butylsulfanyl)methyl]benzenes

Kazuhiro Kobayashi* and Yuuho Shigemura

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A convenient method for the preparation of 1-aryl-1,3-dihydrobenzo[c]thiophenes has been developed using a three-step sequence starting from 2-[aryl(methoxy)methyl]benzyl alcohols. Thus, treatment of the starting materials with thionyl chloride gives the corresponding benzyl chlorides, which are allowed to react with sodium tert-butyl mercaptide to yield 1-[aryl(methoxy)methyl]-2-[(tert-butylsulfanyl)methyl]benzenes. Finally, these compounds undergo cyclization on treatment with concentrated hydrobromic acid to provide the desired products in reasonable yields.