Thionyl Chloride → Methyl 6-(chloromethyl)nicotinate

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Reaction Steps

Thionyl chloride (5.0 ml, 2.0 eq) was added dropwise to a solution of alcohol (III, 5.7 g) in anhydrous chloroform (50 mL) cooling with a water bath. The resulting solution was stirred at room temperature for 2 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution followed by CH2Cl2 extractions. The combined organic layers were dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and then passed through a silica gel pad (eluent 5% MeOH in CH2Cl2) to afford the desired product (7.0 g, 90%) as a off-white solid. MS-ESI m/z 186.09 (M+H)+; 1H NMR (CDCl3) δ 9.18 (d, J=2 Hz, 1H), 8.35 (dd, J=2 and 8.5 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 4.74 (s, 2H), 3.98 (s, 3H) ppm.

Provenance & Evidence