Aniline → 5-Chloro-2-nitrodiphenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-fluoro-1-nitrobenzene (983 mg, 5.60 mmol) and aniline (1.0 mL, 11.20 mmol) in DMSO (3 mL) was heated at 110° C. for 4 h. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with a saturated aqueous solution of KHSO4 (×3), followed by brine, then dried (Na2SO4) and concentrated in vacuo to afford the title compound as an orange solid (1.37 g, 98%). 1H NMR (CDCl3, 400 MHz): δ 9.54 (1H, s), 8.16 (1H, d, J=9.13 Hz), 7.46 (2H, t, J=7.61 Hz), 7.32-7.22 (3H, m), 7.14 (1H, d, J=2.14 Hz), 6.72 (1H, dd, J=9.12, 2.15 Hz)

Provenance & Evidence