反应详情

温度

82 °C

Equip a 5-L, three-neck, round-bottom flask with a large blade mechanical stirrer, thermocouple, an addition funnel, Claisen adapter, reflux condenser, and a sodium hydroxide scrubber. Charge the flask with 2,5-dimethoxycinnamic acid (182.3 g, 865 mmol, 1.0 equiv) and dichloroethane (2.5 L). Add boron tribromide (163.5 mL, 433.2 g, 1.73 mol, 2.0 equiv.) dropwise over 1 h, keeping the temperature below 35° C. Gas evolution can be monitored as the temperature of the reaction is gradually increased to reflux (82° C.). Reflux for 12 h, cool to 5° C., and quench by the careful addition of water (1.0 L). Filter the resulting yellow-red suspension/emulsion through a glass frit and wash with dichloroethane (1.0 L) and heptane (1.0 L) to afford a brown solid. Dry the wet material in a vacuum oven (30 in., 35° C.) for 18 h, to afford the coumarin (180.3 g, 127% theory) as a brown solid: 1H NMR (300 MHz, DMSO-d6) δ 7.97 (d, J=9.6 Hz, 1H), 7.22 (d, J=9.9 Hz, 1H), 7.05 (m, 2H), 6.43 (d, J=9.6 Hz, 1H).

1. temperaturethermocouple, an addition funnel, Claisen adapter, reflux condenser
2. customthe temperature below 35° C
3. temperatureis gradually increased
4. temperatureReflux for 12 h
5. temperaturecool to 5° C.
6. customquench by the careful addition of water (1.0 L)
7. filtrationFilter the resulting yellow-red suspension/emulsion through a glass frit
8. washwash with dichloroethane (1.0 L) and heptane (1.0 L)
9. customto afford a brown solid
10. customDry the wet material in a vacuum oven (30 in., 35° C.) for 18 h