Novel and simple synthesis of brominated 1,10-phenanthrolines

0428953 - ÚMCH 2015 RIV AU eng J - Journal Article
Výprachtický, Drahomír - Kaňková, Dana - Pokorná, Veronika - Kmínek, Ivan - Dzhabarov, Vagif - Cimrová, Věra
Novel and simple synthesis of brominated 1,10-phenanthrolines.
Australian Journal of Chemistry. Roč. 67, č. 6 (2014), s. 915-921. ISSN 0004-9425. E-ISSN 1445-0038
R&D Projects: GA ČR GAP106/12/0827; GA ČR(CZ) GA13-26542S
Institutional support: RVO:61389013
Keywords : 1,10-phenanthroline * electrophilic aromatic substitution * bromination
Subject RIV: CD - Macromolecular Chemistry
Impact factor: 1.558, year: 2014

A novel, simple, and reasonably efficient synthesis of 3,8-dibromo-1,10-phenanthroline, 3,6-dibromo-1,10-phenanthroline, 3,5,8-tribromo-1,10-phenanthroline, and 3,5,6,8-tetrabromo-1,10-phenanthroline is presented herein. The crucial role of a new catalyst (sulfur dichloride – SCl2) for the bromination of 1,10-phenanthroline is reported. The bromination of 1,10-phenanthroline monohydrate in the presence of SCl2 and pyridine yielded the brominated compounds, previously only possible through the complicated multi-step and tedious Skraup synthesis method. The application of the bromination catalyst SCl2 as a medium-strength Lewis acid is demonstrated for the first time, and the results are compared with the behaviours of known weak (sulfur chloride – S2Cl2) and strong (thionyl chloride – SOCl2) bromination catalysts. A reaction mechanism was proposed.
Permanent Link: http://hdl.handle.net/11104/0234867