2-Bromomethyl-6-chloro-4-(trifluoromethyl)pyridine synthesis

Yield:862120-75-0 70%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethane; for 16 h;Heating / reflux;

Steps:

2-(bromomethyl)-6-chloro-4-(trifluoromethyl)pyridine. (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) (164mg, 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) δ7.59 (s, 1H), 7.47 (s, 1H), 4.52 (s, 2H).

References:

US2008/27056,2008,A1 Location in patent:Page/Page column 26