反应 #2271675

反应方程式

water

1,3-dibromopropane

3-hydroxy-4-methoxybenzophenone

sodium hydride

dimethylformamide

→

3-(3-bromopropoxy-4-methoxyphenyl]phenylmethanone

反应条件

后处理

1. 1
   其他At the end of the reaction
2. 2
   萃取extracted with ethyl acetate (400 ml)
3. 3
   洗涤The ethyl acetate solution was washed with water, brine
4. 4
   干燥dried over anhydrous MgSO4
5. 5
   其他The solvent was removed
6. 6
   其他the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g: eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane:dichloromethane, 1.4 l)
7. 7
   其他The pure product thus obtained
8. 8
   其他Recrystallization twice from isopropyl ether (500 ml)

实验过程

A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide, (35 ml) was treated with sodium hydride (600 mg, 25 Mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for 2 hours. At the end of the reaction, the mixture was poured into water (500 ml) and extracted with ethyl acetate (400 ml). The ethyl acetate solution was washed with water, brine, and dried over anhydrous MgSO4. The solvent was removed and the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g: eluted with 3:1 hexane:dichloromethane, 1.6 l; 3:7 hexane:dichloromethane, 1.4 l). The pure product thus obtained weighed 4.67 g, (66%) as an oil. Recrystallization twice from isopropyl ether (500 ml) gave analytically pure 3-(3-bromopropoxy-4-methoxyphenyl]phenylmethanone (2.42 g), m.p.=81°-83° C.

来源