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A general synthetic route to 4‐substituted‐2,2′‐bithiophenes
Author(s) -
Rasmussen Seth C.,
Pickens Jason C.,
Hutchison James E.
Publication year - 1997
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570340143
Subject(s) - chemistry , adduct , grignard reagent , reagent , hydroxymethyl , halogen , organic chemistry , combinatorial chemistry , alkyl
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).