反応 #48100

反応方程式

(5-bromo-2-chloro-phenyl)-(4-methoxy-phenyl)-methanone

triethylsilane

potassium hydroxide

triethylsilane

boron trifluoride etherate

boron trifluoride etherate

→

1-Bromo-4-chloro-3-(4-methoxy-benzyl)-benzene

溶媒

dichloromethane

acetonitrile

water

反応条件

後処理

1. 1
   workup.ADDITIONare added so that the temperature
2. 2
   その他does not exceed 20° C
3. 3
   workup.ADDITIONare added
4. 4
   温度cooled to ambient temperature
5. 5
   その他The organic phase is separated
6. 6
   抽出the aqueous phase is extracted another three times with diisopropylether
7. 7
   洗浄The combined organic phases are washed twice with 2 M potassium hydroxide solution and once with brine
8. 8
   乾燥dried over sodium sulfate
9. 9
   その他After the solvent is evaporated
10. 10
    洗浄the residue is washed with ethanol
11. 11
    その他dried at 60° C.

実験手順

A solution of 86.2 g (5-bromo-2-chloro-phenyl)-(4-methoxy-phenyl)-methanone and 101.5 mL triethylsilane in 75 mL dichloromethane and 150 mL acetonitrile is cooled to 10° C. Then with stirring 50.8 mL of boron trifluoride etherate are added so that the temperature does not exceed 20° C. The solution is stirred for 14 h at ambient temperature, before another 9 mL triethylsilane and 4.4 mL boron trifluoride etherate are added. The solution is stirred for a further 3 h period at 45-50° C. and then cooled to ambient temperature. A solution of 28 g potassium hydroxide in 70 mL water is added and the resultant mixture is stirred for 2 h. The organic phase is separated and the aqueous phase is extracted another three times with diisopropylether. The combined organic phases are washed twice with 2 M potassium hydroxide solution and once with brine and then dried over sodium sulfate. After the solvent is evaporated, the residue is washed with ethanol and dried at 60° C.

出典