Silica gel-assisted preparation of 2,4,7-trihalobenzo[b]thiophenes and 4,7-dihalobenzo[b]thiophenes

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

研究成果: Article査読

2 被引用数 (Scopus)

抄録

All 6 isomers of (bromo)(chloro)(iodo)benzo[b]thiophenes containing three different halogen atoms at the 2-, 4- and 7-positions were synthesized from the corresponding 2-(1-adamantylsulfanyl)-1,4-dihalo-3-(haloethynyl)benzene derivatives, through treatment with silica gel under thermal conditions. In contrast to our previous method using gold chloride catalyst, migration of adamantyl group did not occur in this method using silica gel. Moreover, by using this method, we synthesized 6 types of 4,7-dihalobenzo[b]thiophenes in 4 steps from 2-fluoro-3,6-dihalo-benzaldehydes in moderate to excellent overall yields, 42–82%.

本文言語English
ページ(範囲)768-770
ページ数3
ジャーナルPhosphorus, Sulfur and Silicon and the Related Elements
194
7
DOI
出版ステータスPublished - 2019 7 3

ASJC Scopus subject areas

  • 生化学
  • 有機化学
  • 無機化学

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