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Paper | Regular issue | Vol 96, No. 9, 2018, pp.1529-1548
Published online, 21st August, 2018
DOI: 10.3987/COM-18-13937
Silica Gel-Assisted Preparation of (Bromo)(Chloro)(Iodo)benzo[b]thiophenes Bearing Halogen Atoms at the 2-, 4-, and 7-Positions

Shinichi Mikami, Hiroki Tanaka, Hiroki Kishi, Shuhei Yoshida, and Kozo Toyota*

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


Six types of (bromo)(chloro)(iodo)benzo[b]thiophenes bearing halogen atoms at the 2-, 4-, and 7-positions were prepared from the corresponding 2-(1-adamantylsulfanyl)-1,4-dihalo-3-(haloethynyl)benzene derivatives, by treatment with silica gel under thermal conditions. 4,7-Dihalobenzo[b]thiophenes, bearing two different halogen atoms (chlorine, bromine, or iodine), were also prepared from 2-(1-adamantylsulfanyl)- 3-(ethynyl)-1,4-dihalobenzene derivatives.