反应详情

温度

80 °C

A mixture of ethyl 2-fluoro-5-nitrobenzoate (1.07 g), phenol (565 mg), potassium carbonate (1.38 g) and N,N-dimethylformamide (20 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→30:70). The object fraction was concentrated under reduced pressure and ethanol (20 mL) and 10% palladium on carbon (1.5 g) were added to the residue (1.54 g). The mixture was stirred overnight under a hydrogen stream. The catalyst was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→50:50) and recrystallized from diisopropyl ether-hexane to give the title compound (1.07 g) as a pale-brown powder.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionWater was added to the residue
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→30:70)
8. concentrationThe object fraction was concentrated under reduced pressure and ethanol (20 mL) and 10% palladium on carbon (1.5 g)
9. additionwere added to the residue (1.54 g)
10. stirringThe mixture was stirred overnight under a hydrogen stream
11. filtrationThe catalyst was filtered off
12. concentrationthe filtrate was concentrated
13. customThe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=20:80→50:50)
14. customrecrystallized from diisopropyl ether-hexane