Thionyl Chloride → HCID 23028696, compound

Participants

Reaction Steps

A chloroform (10 ml) solution of (2-fluoropyridin-3-yl)methanol (49 mg, 0.385 mmol) and thionyl chloride (0.14 ml, 1.93 mmol) was stirred at 50° C. for 3.5 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was dissolved in butanol (5 ml), followed by the addition of sodium 4-chlorobenzenesulfinate (92 mg, 0.462 mmol) and potassium acetate (76 mg, 0.770 mmol). The mixture was stirred at 70 to 80° C. for 12 hours. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed successively with a saturated aqueous solution of sodium bicarbonate and brine, and then, dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column. The fraction obtained from the hexane:ethyl acetate (=2:1) eluate was concentrated under reduced pressure, whereby the title compound (59 mg, 54%) was obtained as a white solid.

Provenance & Evidence