Aniline → (3-Fluoro-2-methoxy-6-nitrophenyl)phenylamine

Participants

Reaction Steps

A solution of 1,3-difluoro-2-methoxy-4-nitrobenzene (1 g, 5.29 mmol) and aniline (0.53 mL, 5.82 mmol) in DMSO (10 mL) was heated at 100° C. for 4 h. The reaction mixture was diluted with water and the product extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, eluting with 0-50% Et2O in cyclohexane) to yield the title compound as an off white solid (1.05 g, 76%). 1H NMR 400 MHz δ (CDCl3): 8.82 (1H, br s), 7.96 (1H, dd, J=9.5, 5.3 Hz), 7.32-7.26 (2H, m), 7.12-7.07 (1H, m), 7.02-6.98 (2H, m), 6.74 (1H, t, J=9.5 Hz), 3.53 (3H, d, J=1.1 Hz).

Provenance & Evidence