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Paper | Regular issue | Vol 94, No. 9, 2017, pp.1707-1717
Published online, 28th July, 2017
DOI: 10.3987/COM-17-13767
An Efficient Synthesis of 1-Arylbenzo[c]thiophenes via the Reaction of 2-(Chloromethyl)phenyllithiums with Aromatic Aldehydes

Kazuhiro Kobayashi,* Yuuya Honda, and Yuuho Shigemura

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

Abstract

A simple and efficient sequence for the preparation of 1-arylbenzo[c]thiophenes has been developed. Thus, 2-(chloromethyl)phenyllithiums, generated by treating 2-(chloromethyl)phenyl bromides with butyllithium, are allowed to react with aromatic aldehydes to afford the corresponding diarylmethanol derivatives. These alcohols are oxidized with pyridinium chlorochromate (PCC) to give aryl[(2-chloromethyl)phenyl]methanones, of which treatment with sodium hydrogensulfide gives 1-aryl-1,3-dihydrobenzo[c]thiophen-1-ols. Dehydration of these crude alcohols to the desired products can be accomplished by the treatment with a catalytic amount of p-toluenesulfonic acid.