Methanesulfonyl chloride → 6-Chloro-2-fluoro-3-methanesulfonyl-pyridine

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-fluoropyridine (500 mg, 3.8 mmol) was taken up in tetrahydrofuran (19 mL) and cooled to −78° C. n-Butyllithium (2.4 mL, 3.8 mmol) was added dropwise over 10 minutes. The solution was stirred for 30 minutes and methanesulfonyl chloride (0.3 mL, 3.8 mmol) was added dropwise over 15 minutes. The resulting mixture was stirred at −78° C. for 2 hours and then warmed to 0° C. and stirred for 2 hours followed by an additional 2 hours at room temperature. The reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (silica, 0-75% ethyl acetate/hexanes) to afford the title compound as a light yellow oil.

Provenance & Evidence