Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
BASTOS, Mônica M. et al. Reductive debromination of 1-methyl-2,4,5-tribromoimidazole mediated by dry tetramethylammonium fluoride in aprotic solvents. J. Braz. Chem. Soc. [online]. 2001, vol.12, n.3, pp. 417-421. ISSN 1678-4790. http://dx.doi.org/10.1590/S0103-50532001000300015.
The reaction of dry tetramethylammonium fluoride (TMAF) with 1-methyl-2,4,5-tribromoimidazole in different polar aprotic solvents was investigated. Products of reductive debromination were obtained rather than fluorine substitution, indicating that TMAF is strongly basic in such conditions. A reaction carried out in d6-DMSO showed that the solvent is the proton source. Dimethylformamide was less effective that DMSO, N,N-dimethylacetamide or N-methylpirrolidone as a proton donor and we were able to effect significant fluorination in this solvent.
Keywords : tribroimidazole; fluoroimidazole; reductive debromination.