反应详情

温度

100 °C

A mixture of 4-bromo-3-fluoro(trifluoromethoxy)benzene (6.6 g, 26 mmol), benzophenone imine (6.4 mL, 38 mmol), Pd2(dba)3 (0.58 g, 0.64 mmol), Xantphos (1.5 g, 2.6 mmol) and sodium tert-butoxide (3.7 g, 38 mmol) in 1,4-dioxane (120 mL) was stirred at 100° C. under N2 atmosphere for 5 h. After stirring at room temperature overnight, the mixture was concentrated under reduced pressure. The residue was partitioned between AcOEt and water. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (0/100-5/95 AcOEt/hexane) to give a yellow oil. The residual oil was dissolved in THF (150 mL), and 1 M HCl aqueous solution (50 mL) was added to the mixture. After stirring at room temperature for 1 h, the mixture was basified with 8 M NaOH aqueous solution and extracted with diethyl ether. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel (0/100-5/95 AcOEt/hexane) to give the title compound (4.2 g, 85% yield) as a pale yellow oil: 1H NMR (300 MHz, DMSO-d6): δ ppm 5.36 (2H, s), 6.75-6.85 (1H, m), 6.89-6.94 (1H, m), 7.12 (1H, dd, J=11.7, 2.3 Hz).

1. stirringAfter stirring at room temperature overnight
2. concentrationthe mixture was concentrated under reduced pressure
3. customThe residue was partitioned between AcOEt and water
4. washThe organic layer was washed with brine
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was chromatographed on silica gel (0/100-5/95 AcOEt/hexane)
9. customto give a yellow oil
10. stirringAfter stirring at room temperature for 1 h
11. extractionextracted with diethyl ether
12. washThe organic layer was washed with brine
13. dry with materialdried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated under reduced pressure
16. customThe residue was chromatographed on silica gel (0/100-5/95 AcOEt/hexane)