反应详情

温度

110 °C

4-Bromo-3-fluoroaniline (13.3 g, 70.0 mmol), ethyl acrylate (9.48 mL, 87.5 mmol) and tris(2-methylphenyl)phosphine (8.52 g, 28.0 mmol) were dissolved in N,N-diisopropylethylamine (50 mL) and N,N-dimethylformamide (50 mL), palladium(II) acetate (0.786 g, 3.50 mmol) was added, and the mixture was stirred under an argon atmosphere at 110° C. for 5 hr. After cooling the reaction mixture, the solvent was evaporated under reduced pressure. Water and ethyl acetate were added to the residue, and the insoluble material was removed by filtering through celite. The organic layer in the filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane) to give the title compound (14.0 g, yield 96%). A part thereof was recrystallized to give yellow prism crystals.

1. temperatureAfter cooling the reaction mixture
2. customthe solvent was evaporated under reduced pressure
3. additionWater and ethyl acetate were added to the residue
4. customthe insoluble material was removed
5. filtrationby filtering through celite
6. washThe organic layer in the filtrate was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (20%-60% ethyl acetate/hexane)