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Merck

Synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of didodecyl[1]benzothieno[3,2-b][1]benzothiophenes.

The Journal of organic chemistry (2013-07-16)
Christian Ruzié, Jolanta Karpinska, Alan R Kennedy, Yves H Geerts
RESUMO

The synthesis of 1,6-, 2,7-, 3,8-, and 4,9-isomers of dibromo- and didodecyl[1]benzothieno[3,2-b][1]benzothiophenes, via the stilbene pathway, is described. Starting from the synthesis of bromo-2-(methylthio)benzaldehydes, a series of functionalization, McMurry coupling, and finalising cyclization reactions were explored. The stereochemistry of the cyclization mechanism was investigated. Using this methodology didodecyl[1]benzothieno[3,2-b][1]benzothiophenes were formed in overall yields of 5-32%.

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Sigma-Aldrich
5-Bromo-2-fluorobenzaldehyde, 97%