反应详情

A mixture of dimethyl 4-bromoisophthalate (54.75 g., 200.5 mmol), water (330 ml), tributylamine (55.63 g., 300.7 mmol), 4-fluorostyrene (55.63 g., 300.7 mmol) and bis(triphenylphoshine)palladium(II)chloride (2.81 g., 4.01 mmol) was heated at reflux with stirring under an inert atmosphere for 6 hours. The reaction was cooled to ambient temperature and acidified to pH 2 with 2M HCl (700 ml). The aqueous layer was removed and the residual solid washed with water (2 L), dissolved in dichloromethane (1 L) and passed through a pad of silica, eluting with more dichloromethane (2 L). Evaporation of the dichloromethane gave a solid, which was further washed with iso-hexane (1 L), and dried to give methyl 4-[2-(4-fluorophenyl)ethenyl]-3-methoxycarbonylbenzoate (56.75 g) as a pale yellow solid.

1. temperaturewas heated
2. temperatureat reflux
3. customThe aqueous layer was removed
4. washthe residual solid washed with water (2 L)
5. dissolutiondissolved in dichloromethane (1 L)
6. washeluting with more dichloromethane (2 L)
7. customEvaporation of the dichloromethane
8. customgave a solid, which
9. washwas further washed with iso-hexane (1 L)
10. customdried