Course of bromination of thiazole and 2-methylthiazole

Bromination of thiazole by bromine in the presence of aluminum chloride in neutral solvent or without solvent takes place at the 2-position. Such an orientation contradicts the traditional addition-cleavage mechanism, and agrees with the ylid mechanism of electrophilic substitution. 2-Methylthiazole brominates at the 5-position, and the reaction is impeded in the presence of aluminum chloride; this is due to heterocycle deactivation by complexation with the Lewis acid at the nitrogen atom.Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 837–840, June, 1986.