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Regioselective symmetrical bromination of protected 2,2′-biimidazole

✍ Scribed by David Sanchez-Garcia; Salvador Borros; Santi Nonell; Jose I. Borrell; Carles Colominas; Jordi Teixido

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
29 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Treatment of the benzyl and (trimethylsilylethoxymethyl) SEM protected 2,2′‐biimidazoles, 2a and 2b, with 2 equivalents of N‐bromosuccinimide (NBS) allows obtaining the 5,5′‐dibromo and 4,4′‐dibromo substituted biimidazoles, 3a and 5b respectively. The use of 4 equivalents of NBS, followed by treatment of the corresponding tetrabromoderivatives 4a and 5b with butyl lithium (BuLi), yields the 4,4′‐dibromoderiva‐tives 5a (G=Bn) and 5b (G=SEM).

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