Aniline → Acetic acid 6-fluoro-3-nitro-2-phenylaminobenzyl ester

Participants

Reaction Steps

A solution of acetic acid 2,6-difluoro-3-nitrobenzyl ester (3 g, 12.9 mmol) and aniline (1.5 mL, 16.9 mmol) in DMSO (10 mL) was heated at 100° C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc (3×15 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-100% EtOAc in cyclohexane) to give the title compound as a brown oil (3.2 g, 81%). 1H NMR 400 MHz 6 (CDCl3): 8.21 (1H, dd, J=9.4, 5.9 Hz), 7.30-7.24 (2H, m), 7.10-7.04 (1H, m), 6.97-6.92 (2H, m), 6.83 (1H, dd, J=9.3, 8.4), 4.93 (2H, d, J=2.0 Hz), 1.94 (3H, s)

Provenance & Evidence