
%0 Journal Article
%A Boulton, BE 
%A Coller, BAW 
%T Kinetics, stoichiometry and mechanism in the bromination of aromatic heterocycles. II. Aqueous bromination of imidazole, 1-methylimidazole and 2-methylimidazole
%J Australian Journal of Chemistry
%D 1974/11/01
%V 27
%N 11
%P 2331-2341
%K 
%R https://doi.org/10.1071/CH9742331
%U https://www.publish.csiro.au/paper/CH9742331 
%X The coulo-chrono-potentiometric method has been used to obtain rate constants for reaction of molecular bromine with neutral imidazoles (aq., 298 K). Values of 10-6kbl/dm3 mol-1 s-l were:     Substrate        5-position     4-position    2-position Imidazole        0.5        0.4        0.2 1-Methylimidazole   2.3        1.7        0.8 2-Methylimidazole    90        -         -   The network of reactions leading to 2,4,5-tribromo-1-methylimidazole is described in detail. Relative rates of successive brominations are pH sensitive and conditions may be designed to obtain optimum yields of partially brominated imidazoles. 
