反应详情

温度

-78 °C

LiHMDS (1.0M in THF, 12.9 mL, 12.9 mmol) was added dropwise to a stirred solution of aniline (633 mg, 6.79 mmol) in anhydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 10 min stirring at −78° C., a solution of 1,3-difluoro-2-methyl-4-nitrobenzene (1.12 g, 6.47 mmol) in THF (5 mL) was added and stirring was continued for 30 min. The reaction mixture was quenched by addition of water and was diluted with EtOAc. The resulting emulsion was filtered through Celite® and the organic fraction separated, washed with brine and dried (MgSO4). The volatiles were removed in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane) to afford the title compound (1.5 g, 94%). 1H NMR (CDCl3, 400 MHz): δ 8.74 (1H, br s), 8.07 (1H, dd, J=9.34, 5.86 Hz), 7.30-7.23 (2H, m), 7.03 (1H, t, J=7.41 Hz), 6.85-6.78 (3H, m), 1.92 (3H, d, J=2.87 Hz).

1. stirringstirring
2. waitwas continued for 30 min
3. customThe reaction mixture was quenched by addition of water
4. additionwas diluted with EtOAc
5. filtrationThe resulting emulsion was filtered through Celite®
6. customthe organic fraction separated
7. washwashed with brine
8. dry with materialdried (MgSO4)
9. customThe volatiles were removed in vacuo
10. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane)