Azobisisobutyronitrile → 2-(Bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

(2-chloro-6-methyl-4-(trifluoromethyl)pyridine (10.0 g, 51 mmol), N-bromosuccinimide (10.9 g, 61 mmol), and 2,2′-azobis(2-methylpropionitrile) (164 mg, 1 mmol) were combined in carbon tetrachloride (200 mL) and heated to reflux. After 16 h, the reaction mixture was cooled to 0° C. and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (100% hexanes) to produce 9.1 g (70%) as a light yellow oil. 1H-NMR (CDCl3, 400 MHz) δ 7.59 (s, 1H), 7.47 (s, 1H), 4.52 (s, 2H).

Provenance & Evidence