Methanol → Methyl 2,5-Dichloronicotinate

Participants

Reaction Conditions

Reaction Steps

A solution of 2,5-dichloronicotinic acid (20 g, 0.10 mol) [OChem, 782D853] in dichloromethane (520 mL) was treated with 2 M oxalyl chloride in dichloromethane (160 mL, 310 mmol) followed by a few drops of N,N-dimethylformamide and stirred at 20° C. for 15 hours. The reaction mixture was concentrated, diluted with dichloromethane (200 mL), cooled to 0° C., treated with methanol (110 mL, 2.7 mol), and stirred at 0° C. for 5 minutes. The reaction mixture was concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (0-80%) gave the desired product (19 g, 89%). LCMS calculated for C7H6Cl2NO2 (M+H)+: m/z=206.0, 208.0. found: 205.8, 207.7.

Provenance & Evidence