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Paper | Regular issue | Vol 100, No. 11, 2020, pp.1763-1784
Published online, 15th September, 2020
DOI: 10.3987/COM-20-14302
Synthesis of 4,7-Dibromobenzo[b]thiophene Derivatives via 2-(1-Adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)benzenes and Their Reactions

Kozo Toyota,* Shinichi Mikami, Hiroki Tanaka, Shuhei Yoshida, Kazuma Iwai, Kenta Takahashi, Hiroki Kishi, Yota Kikuchi, Koya Saito, Homa Yamaguchi, and Hirotaka Mutoh

*Department of Chemistry, Graduate School of Science, Tohoku University, Aoba-ku, Sendai 980-8578, Japan

Abstract

Mild Corey-Fuchs reaction conditions using dimethyl sulfoxide - aqueous KOH solution at room temperature were applied to preparation of 2-(1-adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)benzene. Various substituents were introduced to the terminal alkyne moiety of the (ethynyl)(sulfanyl)benzene, either by substitution reaction or by Sonogashira cross coupling. The alkynes thus obtained were converted to the corresponding 4,7-dibromobenzo[b]thiophene derivatives by the ‘silica gel-assisted cyclization method. Reactions of 4,7-dibromobenzo[b]thiophene and 2,4,7-tribromobenzo[b]thiophene were also investigated.