Aniline → 5-Fluoro-2-nitro-N-phenylaniline

Participants

Reaction Steps

LiHMDS (1.0M in THF, 12.57 mL) was added dropwise to a stirred solution of phenylamine (600 μL, 6.60 mmol) in ahydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 30 min, a solution of 2,4-difluoro-1-nitrobenzene (690 μL, 6.29 mmol) in THF (10 mL) was added and stirring was continued for 1 h. The solution was poured into an aqueous solution of NH4Cl (100 mL) and extracted with EtOAc (×3). The combined organic layers were dried and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) affording (5-Fluoro-2-nitrophenyl)phenylamine as a yellow/orange solid (1.37 g, 94%). 1H NMR (CDCl3, 400 MHz): δ 9.66 (1H, s), 8.28 (1H, dd, J=9.48, 6.01 Hz), 7.47 (2H, t, J=7.63 Hz), 7.36-7.24 (3H, m), 6.82 (1H, dd, J=11.38, 2.61 Hz), 6.53-6.44 (1H, m).

Provenance & Evidence