Azobisisobutyronitrile → 2,6-Dichloro-3-nitrobenzyl Bromide

Participants

Reaction Steps

To a solution of 1,3-dichloro-2-methyl-4-nitro-benzene (19) (6.18 g, 30 mmol) and AIBN (200 mg) in CCl4 (75 mL), NBS (7.96 g, 45 mmol) was added under stirring and reflux. The reaction was monitored by 1H-NMR (CDCl3). Additional NBS (5×7.96 g, total of 270 mmol) was added till the starting material was consumed. The reaction mixture was filtered hot, and the filtrate was evaporated to dryness. The crude was column chromatographed (SiO2, hexanes:EtOAc, 9:1 to 8.5:1.5). The product was obtained as a low melting white solid: yield 6.869 g, 80%. 1H-NMR (CDCl3) δ 4.75 (s, 2H), 7.45, d, 1H, J=8.5 Hz), 7.69 (d, 1H, J=8.5 Hz); MS (CI) m/z 285 (M+H). Anal Calcd for C7H4BrCl2NO2 : C, 29.51; H, 1.42; N, 4.92. Found: C, 29.09; H, 1.43; N, 4.71.

Provenance & Evidence