Azobisisobutyronitrile → 5-Bromo-2-(bromomethyl)pyrimidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-methylpyrimidine (119) (1.34 g, 7.75 mmol), N-bromosuccinimide (1.40 g, 7.87 mmol) and AIBN (0.13 g, 0.79 mmol) in CCl4 (15 mL) was stirred at 60° C. for 3 h. The resulting mixture was filtered, the filter cake was washed with Et2O (100 mL), and the combined filtrates were concentrated under reduced pressure. Column chromatography of the residue, eluting with 2:1 EtOAc:hexanes, gave 5-bromo-2-(bromomethyl)pyrimidine (120) (0.214 g, 11%) as a white solid: mp 55-57° C.; 1H NMR (CDCl3) δ 8.79 (s, 2H), 4.57 (s, 2H). Anal. (C5H4Br2N2) C, H, N.

Provenance & Evidence