4-Fluoroaniline → HCID 54527561, compound

Participants

Reaction Conditions

Reaction Steps

4-Fluorophenylamine (1.47 g, 13.19 mmol) was dissolved in THF (20 mL) and cooled to −70° C., under an atmosphere of nitrogen. A solution of 1M LiHMDS in THF (25.14 mL, 25.14 mmol) was added dropwise and the mixture stirred at −70° C., under an atmosphere of nitrogen for 15 minutes. A solution of 2,4-difluoronitrobenzene (2.0 g, 12.57 mmol) in THF (10 mL) was added dropwise to the mixture, at −70° C. and the resultant purple solution stirred at −70° C. for 30 min. The reaction mixture was quenched with saturated aqueous NH4Cl solution and extracted into EtOAc (3×50 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, gradient 0-100% DCM in cyclohexane) to afford the title compound as an orange solid (2.94 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 9.53 (1H, s), 8.27 (1H, dd, J=9.48, 5.98 Hz), 7.29-7.22 (2H, m), 7.20-7.11 (2H, m), 6.64 (1H, dd, J=11.26, 2.65 Hz), 6.48 (1H, ddd, J=9.47, 7.12, 2.65 Hz)

Provenance & Evidence