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A general synthetic route to 4-substituted-2,2′-bithiophenes

✍ Scribed by Seth C. Rasmussen; Jason C. Pickens; James E. Hutchison

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
341 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new synthetic route to 4‐substituted‐2,2′‐bithiophenes has been developed utilizing 4‐bromo‐2,2′‐bithiophene (1). Formation of the bithienyllithium adduct via halogen‐metal exchange was found to be problematic and resulted in complex mixtures of products. The Grignard reagent of 1 can be obtained easily via the “entrainment” method, allowing the production of 4‐substituted‐2,2′‐bithiophenes (where sub‐stituent = octyl, hydroxyethyl, hydroxymethyl, carboxy, carbomethoxy, acetoxyethyl, and acetoxymethyl).

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