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Paper | Special issue | Vol 97, No. 2, 2018, pp.1116-1127
Published online, 22nd June, 2018
DOI: 10.3987/COM-18-S(T)94
2-Functionalized Derivatives of 2-Bromo-1,3-dimethylimidazole

Martin Lampl, Gerhard Laus, Klaus Wurst, Volker Kahlenberg, Thomas Gelbrich, Sven Nerdinger,* Hubert Huppertz, and Herwig Schottenberger

*Global Portfolio, Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria

Abstract

Attempts of direct bromination of 1,3-dimethylimidazolium salts with bromine were futile. A tribromide or a carbene–lithium–THF adduct were received instead. The quaternary 2-bromo compound was obtained by methylation of 2‑bromo‑1‑methylimidazole and subsequent ion metathesis, which was converted to the corresponding 2-cyano and 2-azido derivatives. Typical reactions of the latter include a dipolar cycloaddition and the Staudinger reaction. Crystal structures of eight compounds have been determined by single-crystal X-ray diffraction.