反应详情

温度

80 °C

A biphasic solution of 6-acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate (2.537 g, 7.425 mmol) and (3-fluorophenyl)boronic acid (1.56 g, 11.1 mmol) in toluene (70 mL) and 0.8 M sodium hydrogenecarbonate in water (70 mL, 50 mmol) was bubbled with N2 to degas. Tetrakis(triphenylphosphine)palladium(0) (0.429 g, 0.371 mmol) was added. The mixture was degassed with N2 for an additional 5 minutes and then heated at 80° C. for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to a dark solid. The material was dissolved in CHCl3 and was purified on silica gel column, eluting with 0 to 40% ethyl acetate in hexane, to give the desired product (2.105 g, 99%). LCMS calculated for C16H12ClFNO (M+H)+: m/z=288.1; Found: 288.1.

1. customto degas
2. customThe mixture was degassed with N2 for an additional 5 minutes
3. temperatureAfter cooling to room temperature
4. additionthe mixture was diluted with ethyl acetate
5. customThe layers were separated
6. extractionthe aq. layer was extracted with ethyl acetate
7. washThe combined extracts were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated to a dark solid
11. dissolutionThe material was dissolved in CHCl3
12. customwas purified on silica gel column
13. washeluting with 0 to 40% ethyl acetate in hexane