反应详情

温度

100 °C

To a solution of methyl 2-bromo-6-fluorobenzoate (53 g, 0.228 mol) and potassium trifluoro(vinyl)borate (33.63 g, 0.251 mol) in dioxane and H2O (3:1, 600 mL) was added Pd(dppf)Cl2 (5 g, 6.84 mmol) and sodium carbonate (69 g, 0.684 mol) at RT. The reaction mixture was heated at 100° C. for 12 hours under a nitrogen atmosphere. The mixture was concentrated in vacuo, diluted with water, and extracted with EtOAc (3×200 mL). The combined organic layers were washed with brine, dried over anhydrous Na2CO3, filtered, and concentrated. The crude product was purified by column chromatography eluting with a gradient of EtOAc (1-100%) and PE to give the title compound (31.4 g, 76.5%). 1H NMR (400 MHz, CDCl3) δ ppm 7.45-7.36 (m, 2H), 7.03-7.02 (m, 1H), 6.88-6.81 (m, 1H), 5.77-5.73 (m, 1H), 5.41-5.39 (d, J=10.8 Hz, 1H), 3.95 (s, 3H).

1. concentrationThe mixture was concentrated in vacuo
2. additiondiluted with water
3. extractionextracted with EtOAc (3×200 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous Na2CO3
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by column chromatography
9. washeluting with a gradient of EtOAc (1-100%) and PE