反应 #1076758

反应方程式

ammonium chloride

4-(4-(trans-4-pentylcyclohexyl)butyl)cyclohexanone

magnesium

2,3-difluoro-1-bromobenzene

→

1,2-difluoro-3-(4-(4-(trans-4-pentylcyclohexyl)-butyl)cyclohexene-1-yl)benzene

收率 66.4%

溶剂

THF

THF

THF

反应条件

后处理

1. 1
   workup.STIRRINGstirred at 50 to 60° C. for 2 hours
2. 2
   其他to terminate
3. 3
   其他the reaction
4. 4
   过滤The reaction mixture was filtered with Celite
5. 5
   workup.DISTILLATIONthe solvent was distilled off under a reduced pressure
6. 6
   萃取it was extracted with 2.0 l of toluene
7. 7
   洗涤The organic layer was washed with 1.0 l of water thrice
8. 8
   干燥dried over anhydrous magnesium sulfate
9. 9
   其他After the anhydrous magnesium sulfate was removed by filtration, 23.7 g of p-toluenesulfonic acid monohydrate
10. 10
    workup.ADDITIONwas added to the filtrate
11. 11
    温度heated
12. 12
    温度to reflux for 4 hours
13. 13
    洗涤The organic layer was washed with 1.0 l of water thrice
14. 14
    干燥dried over anhydrous magnesium sulfate
15. 15
    workup.DISTILLATIONThe solvent was distilled off under a reduced pressure

实验过程

Under nitrogen gas stream, 52.3 g (2150 mmol) of magnesium was added in 100 ml of THF, and a solution of 378 g (1960 mmol) of 2,3-difluoro-1-bromobenzene in 4.0 l of THF was added by drops thereto so that the reaction temperature was maintained at about 50° C. Further, after stirred at room temperature for 1 hour, a solution of 500 g (1630 mmol) of 4-(4-(trans-4-pentylcyclohexyl)butyl)cyclohexanone in 5.0 l of THF was added by drops to the solution and stirred at 50 to 60° C. for 2 hours, and then 1.0 l of saturated aqueous ammonium chloride solution was added to the solution to terminate the reaction. The reaction mixture was filtered with Celite, the solvent was distilled off under a reduced pressure, and then it was extracted with 2.0 l of toluene. The organic layer was washed with 1.0 l of water thrice and dried over anhydrous magnesium sulfate. After the anhydrous magnesium sulfate was removed by filtration, 23.7 g of p-toluenesulfonic acid monohydrate was added to the filtrate and heated to reflux for 4 hours. The organic layer was washed with 1.0 l of water thrice and dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: heptane) to obtain 436 g of a crude 1,2-difluoro-3-(4-(4-(trans-4-pentylcyclohexyl)-butyl)cyclohexene-1-yl)benzene.

来源