تفاعل #2271675

معادلة التفاعل

water

1,3-dibromopropane

3-hydroxy-4-methoxybenzophenone

sodium hydride

dimethylformamide

→

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

ظروف التفاعل

المعالجة

1. 1
   أخرىAt the end of the reaction
2. 2
   استخلاصextracted with ethyl acetate (400 ml)
3. 3
   غسيلThe ethyl acetate solution was washed with water, brine
4. 4
   تجفيفdried over anhydrous MgSO4
5. 5
   أخرىThe solvent was removed
6. 6
   أخرىthe 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
   أخرىThe pure product thus obtained
8. 8
   أخرىRecrystallization twice from isopropyl ether (500 ml)

الإجراء التجريبي

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.

المصدر