反应详情

A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmol), K2O3 (12.5 g), and 1,3-dibromopropane (15 g, 75 mmol) in acetonitrile (100 ml) was heated at reflux for 3 hours and left standing at room temperature overnight. The solvent of the reaction was removed on a rotary evaporator, and the crude solid was extracted into methylene chloride (500 ml). The insolubles were filtered off. The dichloromethane solution was concentrated and the material was purified on a flash chromatography column (SiO2, 105 g; eluted with 2:3 dichloromethane:hexane, and then with dichloromethane). The desired product thus purified weighed 7.74 g (52%). Recrystallization twice from ethanol gave analytically pure 4-(3-bromopropoxy)-3-methoxybenzonitrile, m.p.=99°-101° C.

1. temperaturewas heated
2. temperatureat reflux for 3 hours
3. waitleft
4. customThe solvent of the reaction was removed on a rotary evaporator
5. extractionthe crude solid was extracted into methylene chloride (500 ml)
6. filtrationThe insolubles were filtered off
7. concentrationThe dichloromethane solution was concentrated
8. customthe material was purified on a flash chromatography column (SiO2, 105 g
9. washeluted with 2:3 dichloromethane
10. customThe desired product thus purified
11. customRecrystallization twice from ethanol