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

Participants

Reaction Steps

A mixture of 1,2-difluoro-3-nitrobenzene (690 μL, 6.29 mmol), phenylamine (600 μL, 6.60 mmol) and potassium carbonate (1.74 g, 12.57 mmol) in DMSO (3 mL) was stirred at RT for 3 h and then heated to 90° C. for 4 h. After cooling to RT, the reaction mixture was partitioned between EtOAc and water. The organic layer was then washed with brine, dried (Na2SO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% EtOAc in cyclohexane) followed by (Si—PCC, gradient 0-50% DCM in cyclohexane) affording (2-Fluoro-6-nitrophenyl)phenylamine as a orange/red oil (563 mg, 39%). 1H NMR (CDCl3, 400 MHz): δ 8.70 (1H, s), 8.00 (1H, d, J=8.66 Hz), 7.36-7.23 (3H, m), 7.09 (1H, t, J=7.41 Hz), 7.03-6.89 (3H, m).

Provenance & Evidence