Hexachloroethane → 3-Bromo-4-chloro-5-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of diisopropylamine (0.48 mL, 0.0034 mol) in dry tetrahydrofuran (10 mL) was added 1.6 M n-butyl lithium in hexane (2.39 mL, 0.00369 mol) drop wise under nitrogen atmosphere at −78° C. and stirred for 30 min at −78° C. To the above stirred mixture was added a solution of 3-bromo-5-fluoropyridine (0.5 g, 0.00284 mol) in dry tetrahydrofuran at −78° C. and stirred for 45 min. After 45 min, a solution of hexachloroethane in dry tetrahydrofuran was added to the above reaction mixture at −78° C. and stirred for 30 min at −78° C. The reaction mixture was slowly warmed to RT and stirred for 1 h. The reaction was quenched with saturated solution of ammonium chloride (10 mL) and extracted with diethyl ether (25 mL x 3). The combined organic layer was washed with water, saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The obtained crude was purified with silica gel chromatography by hexane to afford the title compound. 1H NMR (400 MHz, CDCl3) δ: 8.58 (s, 1H), 8.43 (s, 1H). MS (M+1): 209.9.

Provenance & Evidence