Methyl chloroformate → Methyl 5-chloro-2-nitrobenzoate

Participants

Reaction Steps

To a solution of 10 g (49.6 mmol) of 5-chloro-2-nitrobenzoic acid and 9 mL (64.5 mmol) Et3N in 300 ml CH2Cl2 at 0° C. was added 4.6 mL (59.5 mmol) methyl chloroformate. The cold bath was removed and after 10 minutes, 0.200 mL methanol was added. Bubbles of CO2 could be seen rising from the solution. After 2 hours, the mixture was diluted with Et2O, was washed with 5% HCl, was washed with saturated NaHCO3 solution, was washed with brine, was dried over MgSO4 and decolorized with charcoal, then was stripped of solvent in vacuo to give the product. Rf 0.35 in 15% EtOAc/hexane, visualized by UV; 1H-NMR (400 MHz, CDCl3): δ 7.92 (d, J=8.6 Hz, 1H), 7.69 (d, J=2.3 Hz, 1H), 7.59 (dd, J1 =2.2 Hz, J2 =8.8 Hz, 1H), 3.94 (s, 3H).

Provenance & Evidence