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Note | Regular issue | Vol 81, No. 7, 2010, pp.1703-1709
Published online, 31st May, 2010
DOI: 10.3987/COM-10-11970
■ Synthesis of 3-Substituted Benzo[b]thiophenes via the Reaction of α-Substituted 2-Lithio-β-methoxystyrenes with Sulfur

Kazuhiro Kobayashi,* Daisuke Nakai, Shuhei Fukamachi, and Hisatoshi Konishi

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

Abstract

3-Substitued benzo[b]thiophenes were synthesized in reasonable overall yields from α-substituted 2-bromo-β-methoxystyrenes. Thus, the bromine-lithium exchange between these bromostyrenes with butyllithium in diethyl ether at 0 ˚C followed by reaction with sulfur afforded the corresponding α-substituted β-methoxy-2-sulfanylstyrenes. These were then treated with an equimolar amount of concentrated hydriodic acid in acetonitrile at room temperature to give the desired products.