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Paper | Regular issue | Vol 100, No. 3, 2020, pp.399-417
Published online, 27th February, 2020
DOI: 10.3987/COM-20-14208
2-Bromo-1,3-di(methoxy)imidazolium Tribromide as Starting Salt for 2-Aryl- and 2-Heteroaryl mercapto Derivatives

Lukas Fliri, Sandro Neuner, Martin Lampl, Gabriel Partl, Holger Kopacka, Klaus Wurst, Thomas Gelbrich, Volker Kahlenberg, Sven Nerdinger,* and Herwig Schottenberger*

*Early Stage Development, Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria


A one-pot alkylation/bromination sequence of 1-hydroxyimidazole 3-oxide led to the simple isolation of new 2-bromo-1,3-di(methoxy)imidazolium tribromide 1 by spontaneous precipitation from the aqueous reaction mixture. The related bromide 2, quantitatively and cleanly derived from the tribromide 1 via sacrificial bromination of cyclohexene, as well as the hexafluorophosphate 3,easily accessible through anion metathesis, represent valuable congeners for a rich follow-up chemistry. The reactivity of the 2-bromo substituent towards nucleophilic substitution by different S-nucleophiles was chosen as a startingpoint. Thus, a series of 2-arylmercapto- and 2-hetarylmercaptoimidazolium salts, which are otherwise only elaborately to access, could be isolated with minimal effort. In addition to routine spectroscopic characterization, eleven selected compounds have been determined using single-crystal X-ray diffraction.