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

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).

1. additionUpon mixing
2. customthe layers were separated
3. washthe organic layer was washed with NaCl(sat.) (100 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude material was purified by Silica gel chromatography (0-5% EtOAc/CH2Cl2)

ORD record

ord-03b16be3638841cb97d285432e87cdd7

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173647B2