Hydrogen Bromide → 2,5-Dibromo-3-methylpyridine

Participants

Reaction Steps

5-Bromo-3-methyl-pyridin-2-ylamine (1.0 eq.) was added portionwise to aqueous HBr (48%; 1.0M). The mixture was stirred 1 h at rt then cooled to −20° C. Bromine (2.8 eq.) was added dropwise followed by a aqueous solution of NaNO2 (1.0M; 2.7 eq.). The final mixture was warmed to rt and stirred for 2 h. The mixture was cooled back to −20° C. then aqueous NaOH (1.0M; 3.0 eq.) was added dropwise over 1 h. The final mixture was warmed to rt and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound as a yellow solid.

Provenance & Evidence