反应详情

2-Chloro-1,3-difluoro-4-nitrobenzene (5.37 g, 27.7 mmol), ethanolamine (1.69 g, 27.7 mmol) and Et3N (2.80 g, 27.7 mmol) are stirred in EtOH (40.0 mL) at room temperature for 2 hours. The solvent is then evaporated, and the resulting residue is suspended in EtOAc (50.0 mL) and washed with 0.5 N NaOH (50.0 mL). The aqueous phase is extracted 4 times with EtOAc (4×50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated. The product is purified by flash chromatography on silica gel, eluting with mixtures of heptane and EtOAc (5.53 g, 85%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.39 (dd, J=10.55, 5.27 Hz, 2H) 3.53 (t, J=5.47 Hz, 2H) 4.89 (s, 1H) 6.89 (dd, J=9.37, 8.01 Hz, 1H) 7.19 (t, J=4.69 Hz, 1H) 8.01 (dd, J=9.47, 5.96 Hz, 1H).

1. customThe solvent is then evaporated
2. washwashed with 0.5 N NaOH (50.0 mL)
3. extractionThe aqueous phase is extracted 4 times with EtOAc (4×50.0 mL)
4. dry with materialThe combined organic phases are dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe product is purified by flash chromatography on silica gel
8. washeluting with mixtures of heptane and EtOAc (5.53 g, 85%)