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温度

0 °C

HATU (927 mg, 2.44 mmol), morpholine (0.212 mL, 2.44 mmol), and diisopropylethylamine (0.532 mL, 3.05 mmol) were added sequentially to a solution of 3-bromo-5-nitrobenzoic acid (500 mg, 2.03 mmol) in DMF (10 mL) at 0° C. The reaction mixture was stirred for 2 hours at 0° C., then the mixture was diluted with ethyl acetate (50 mL) and washed with saturated aqueous NaHCO3 (50 mL) followed by 1:1 water: brine (2×30 mL). The organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) provided (3-bromo-5-nitrophenyl)(morpholin-4-yl)methanone as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.43 (t, J=1.9 Hz, 1H), 8.28-8.12 (m, 1H), 7.89 (t, J=1.5 Hz, 1H), 3.74 (br m, 8H).

1. washwashed with saturated aqueous NaHCO3 (50 mL)
2. dry with materialThe organic layers were dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)