反应 #2271688

反应方程式

4-hydroxy-3-methoxybenzonitrile

K2CO3

1.3-dibromopropane

→

4-(3-bromopropoxy)-3-methoxybenzonitrile

溶剂

acetonitrile

反应条件

后处理

1. 1
   温度was heated
2. 2
   温度at reflux for 3 hours
3. 3
   workup.WAITleft
4. 4
   其他The solvent of the reaction was removed on a rotary evaporator
5. 5
   萃取the crude solid was extracted into methylene chloride (500 ml)
6. 6
   过滤The insolubles were filtered off
7. 7
   浓缩The dichloromethane solution was concentrated
8. 8
   其他the material was purified on a flash chromatography column (SiO2, 105 g
9. 9
   洗涤eluted with 2:3 dichloromethane
10. 10
    其他The desired product thus purified
11. 11
    其他Recrystallization twice from ethanol

实验过程

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. ANALYSIS: Calculated for C11H12BrNO2: 48.91%C 4.48%H 5.19%N Found: 49.49%C 4.47%H 5.21%N

来源