反应详情

A solution of isobutylzinc bromide in THF (0.5 M, 30 mL, 15.0 mmol) was added under argon to ethyl 4-bromo-3-chlorobenzoate (D16) (2.00 g, 7.60 mmol) and then 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (930 mg, 1.14 mmol) was added. The reaction was heated to reflux for 4.5 h. The mixture concentrated in vacuo and the residue partitioned between ethyl acetate (125 mL) and water (125 mL). A solid formed, which was filtered off and discarded. The organic layer was washed with water (100 mL), dried (phase separator) and concentrated in vacuo. The crude product was purified by silica chromatography, eluting with 0-5% EtOAc in hexane over 30 minutes to give the title compound as a colourless oil (1.76 g, 7.33 mmol). δH (d6-DMSO, 400 MHz): 7.91 (1H, d), 7.80 (1H, dd), 7.46 (1H, d), 4.30 (2H, q), 2.66 (2H, d), 1.88-2.01 (1H, m), 1.32 (3H, t), 0.89 (6H, d).

1. addition1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (930 mg, 1.14 mmol) was added
2. temperatureThe reaction was heated
3. temperatureto reflux for 4.5 h
4. concentrationThe mixture concentrated in vacuo
5. customthe residue partitioned between ethyl acetate (125 mL) and water (125 mL)
6. customA solid formed
7. filtrationwhich was filtered off
8. washThe organic layer was washed with water (100 mL)
9. customdried (phase separator)
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by silica chromatography
12. washeluting with 0-5% EtOAc in hexane over 30 minutes