Dipropylamine → Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

Participants

Reaction Steps

A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (2.0 g, 7.72 mmol) and HATU (3.52 g, 9.27 mmol) in DMF (70 mL) was stirred at room temperature for 10 min. Then dipropylamine (0.78 g, 1.1 mL, 7.72 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (2.6 g, 99.5% yield): 1H NMR (CD3OD, 500 MHz) δ ppm 0.78 (3H, t, J=5 Hz), 1.01 (3H, t, J=5 Hz), 1.60 (2H, m), 1.74 (2H, m), 3.21 (2H, m), 3.49 (2H, m), 3.96 (3H, s), 7.79 (1H, m), 7.94 (1H, m), 8.23 (1H, m). HPLC retention time: 2.018 min (method B). MS (ESI) (M+H)+ 342.09.

Provenance & Evidence