3-Methoxyaniline → HCID 68157885, compound

Participants

Reaction Steps

A solution of 3-methoxyphenylamine (1.58 g, 12.82 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. This was stirred at −70° C. for 15 minutes before a solution of 2,4-difluoronitrobenzene (2.00 g, 12.57 mmol) in anhydrous THF (10 mL) was added dropwise. The dark yellow solution was then allowed to reach RT and was quenched with saturated aqueous NH4Cl solution. This was extracted into EtOAc (3×) and the combined organic fractions were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a dark yellow gum, which solidified on standing (3.35 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 9.60 (1H, s), 8.25 (1H, dd, J=9.48, 5.99 Hz), 7.34 (1H, t, J=8.00 Hz), 6.90-6.77 (4H, m), 6.47 (1H, ddd, J=9.47, 7.11, 2.64 Hz), 3.83 (3H, s)

Provenance & Evidence