Dichloromethane → 5-Bromo-4-(trifluoromethyl)pyridin-2-amine

Participants

Reaction Steps

To a solution of 2-amino-4-trifluoromethylpyridine (10.0 g, 62.1 mmol) in chloroform (200 mL) was added NBS (12.0 g, 67.4 mmol). The solution was stirred in the dark for 2 hours, at which time it was added to DCM (200 mL) and 1N NaOH (200 mL). Upon mixing, the layers were separated and the organic layer was washed with NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated. The crude material was purified by Silica gel chromatography (0-5% EtOAc/CH2Cl2) yielding 12.0 g (80%) of 5-bromo-4-(trifluoromethyl)-2-pyridylamine: LCMS (m/z): 241/243 (MH+); 1H NMR (CDCl3): δ 8.28(s, 1H), 6.77(s, 1H), 4.78(bs, 2H).

Provenance & Evidence