Dimethylformamide → 4-(2-Chloro-5-fluoro-benzoylamino)-3-methoxy-benzoyl chloride

Participants

Reaction Steps

35 (152 g, 0.45 mol, 1 equiv.) was suspended in dichloromethane (1.5 L) and dimethylformamide (1 mL) was added. Oxalyl chloride (71.6 g, 0.56 mol, 1.2 equiv.) was added drop-wise over 30 minutes at 0° C. After addition, the cold bath was removed and the reaction mixture was further stirred at room temperature for 3.5 h. The solvent and any unreacted oxalyl chloride were evaporated to yield a white solid, which was further dried on a rotary evaporator under vacuum at 40° C. overnight to yield dry 4-(2-chloro-5-fluoro-benzoylamino)-3-methoxy-benzoyl chloride 36 as a white solid. 1H NMR (400 MHz, CDCl3) δ: 8.97 (s, 1H), 8.71 (d, 1H), 7.91 (dd, 1H), 7.60 (d, 1H), 7.57 (dd, 1H), 7.47 (dd, 1H), 7.21-7.15 (m, 1H), 3.99 (s, 3H). MS (ES) m/z 339.9 (MH)+.

Provenance & Evidence