반응 #457335

반응 방정식

4-hydroxy-3-methoxybenzonitrile

K2CO3

1,3-dibromopropane

→

4-(3-bromopropoxy)-3-methoxybenzonitrile

용매

acetonitrile

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux for 3 hours
3. 3
   workup.WAITleft
4. 4
   기타The solvent of the reaction was removed on a rotary evaporator
5. 5
   추출the crude solid was extracted into methylene chloride (500 ml)
6. 6
   여과The insolubles were filtered off
7. 7
   농축The dichloromethane solution was concentrated
8. 8
   기타the material was purified on a flash chromatography column (SiO2, 105 g
9. 9
   세척eluted with 2:3 dichloromethane
10. 10
    기타The desired product thus purified
11. 11
    기타Recrystallization twice from ethanol

실험 절차

A mixture of 4-hydroxy-3-methoxybenzonitrile (7.5 g, 50 mmol), K2CO3 (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.

출처