2-Fluoroaniline → HCID 68157911, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-fluorophenylamine (1.47 g, 13.19 mmol) in anhydrous THF (20 mL) was cooled to −70° C. To this was added dropwise 1M LiHMDS in THF (25.14 mL, 25.14 mmol) over 10 minutes to afford a dark yellow solution. A solution of 2,4-difluoronitrobenzene (2.00 g, 12.57 mmol) in anhydrous THF (10 mL) was added dropwise to the yellow solution, to afford a purple solution. The was stirred at −70° C. for 15 minutes, before being allowed to reach RT. It was then quenched with saturated aqueous NH4Cl solution (25 mL) and extracted into EtOAc (3×50 mL). The combined organic fractions were washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo to afford an orange solid. This was purified by column chromatography (silica gel, gradient 0-100% DCM in cyclohexane) to afford the title compound as a yellow solid (3.04 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 9.36 (1H, s), 8.20 (1H, dd, J=9.45, 5.94 Hz), 7.34-7.26 (1H, m), 7.24-7.10 (3H, m), 6.56 (1H, dt, J=11.09, 2.07 Hz), 6.45 (1H, ddd, J=9.44, 7.13, 2.63 Hz)

Provenance & Evidence