Aniline → (2-Chloro-3-fluoro-6-nitrophenyl)phenylamine

Participants

Reaction Conditions

Reaction Steps

LiHMDS (1.0M in THF, 10.3 mL, 10.3 mmol) was added dropwise to a stirred solution of aniline (505 mg, 5.43 mmol) in anhydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 10 min stirring at −78° C., a solution of 2-chloro-1,3-difluoro-4-nitrobenzene (1.0 g, 5.17 mmol) in THF (5 mL) was added and stirring at −78° C. was continued for 30 min. The reaction mixture was quenched by addition of water then extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-70% EtOAc in cyclohexane) to afford the title compound (1.28 g, 93%). 1H NMR (CDCl3, 400 MHz): δ 8.70 (1H, s), 8.15 (1H, dd, J=9.44, 5.61 Hz), 7.36-7.28 (2H, m), 7.12 (1H, t, J=7.44 Hz), 6.98-6.86 (3H, m).

Provenance & Evidence