Aniline → (2-Bromo-6-nitrophenyl)phenylamine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-bromo-2-fluoro-3-nitrobenzene (5 g, 22.7 mmol) and aniline (4.2 mL, 45 mmol) in DMSO (10 mL, 2M) in a sealed flask was evacuated and purged with argon. The mixture was heated at 100° C. for 12 h. The cooled mixture was diluted with KHSO4 (aq. satd. solution, 100 mL) and brine, dried (Na2SO4) and concentrated to give the product (2-bromo-6-nitrophenyl)phenylamine as a bright orange solid (6.5 g, quant.). 1H NMR (400 MHz, CDCl3): δ 7.96 (1H, dd, J=8.5, 1.7 Hz), 7.86 (1H, br s), 7.75 (1H, dd, J=8.2, 1.5 Hz), 7.16-7.22 (2H, m), 6.90-6.99 (2H, m), 6.77 (2H, m).

Provenance & Evidence