Boron trifluoride etherate → Methyl 3-amino-6-bromo-2-nitrobenzoate

Participants

Reaction Steps

A solution of 3-acetylamino-6-bromo-2-nitro-benzoic acid methyl ester (iii, 5.53 g, 17.42 mmol) and BF3.Et2O (10.0 mL, 78.91 mmol) in MeOH (100 mL) was heated to reflux for 2 h and cooled to room temperature. The reaction mixture was neutralized with solid NaHCO3 and the solvent was removed under reduced pressure. The solid residu was dissolved in EtOAc (400 mL) and washed with H2O (3×200 mL), brine (1×200 mL), and dried with Na2SO4. The solvent was removed under reduced pressure to yield the desired product iv as an orange solid (4.74 g, 100%). 1H NMR (CDCl3): δ 7.40 (d, J=9.3 Hz, 1H), 6.70 (d, J=9.3 Hz, 1H), 6.09 (br s, 2H), 3.90 (s, 3H). Anal. Calcd for C8H7BrN2O4: C, 34.93; H, 2.57; N, 10.18. Found: C, 35.08; H, 2.49; N, 10.06.

Provenance & Evidence