반응 #2271675

반응 방정식

water

1,3-dibromopropane

3-hydroxy-4-methoxybenzophenone

sodium hydride

dimethylformamide

→

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

반응 조건

후처리

1. 1
   기타At the end of the reaction
2. 2
   추출extracted with ethyl acetate (400 ml)
3. 3
   세척The ethyl acetate solution was washed with water, brine
4. 4
   건조dried over anhydrous MgSO4
5. 5
   기타The solvent was removed
6. 6
   기타the 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
   기타The pure product thus obtained
8. 8
   기타Recrystallization twice from isopropyl ether (500 ml)

실험 절차

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.

출처