反应 #1277

反应方程式

3,4-difluorobromobenzene

water

4-(4-propylcyclohexyl)-phenyltrimethoxysilane

TBAF

→

white crystals

收率 94.5%

4-(4-propylcyclohexyl)-3',4'-difluorobiphenyl

收率 94.5%

溶剂

toluene

toluene

toluene

反应条件

后处理

1. 1
   其他After the solvent was removed under reduced pressure
2. 2
   温度The resulting mixture was refluxed for 3 hours
3. 3
   温度After cooling, to the reaction mixture
4. 4
   其他The organic layer was separated
5. 5
   萃取the aqueous layer was extracted with toluene three times
6. 6
   干燥The combined organic layer was dried over magnesium sulfate
7. 7
   其他After the magnesium sulfate was removed by filtration
8. 8
   其他the filtrate was evaporated under reduced pressure
9. 9
   其他The residue was purified by silica gel column chromatography (heptane)

实验过程

To 0.645 g (2 mmol) of 4-(4-propylcyclohexyl)-phenyltrimethoxysilane (Ih) was added 2.1 ml of TBAF (2.1 mmol, 1M in THF) under nitrogen, and the mixture was stirred at room temperature for 30 minutes. After the solvent was removed under reduced pressure, a solution of 3,4-difluorobromobenzene (0.463 g, 2.4 mmol) in toluene (1 ml) was added, followed by the addition of a suspension of tetrakis(triphenylphosphine)palladium(0) (0.116 g, 0.1 mmol) in toluene (3 ml). The resulting mixture was refluxed for 3 hours. After cooling, to the reaction mixture were added water and toluene. The organic layer was separated and the aqueous layer was extracted with toluene three times. The combined organic layer was dried over magnesium sulfate. After the magnesium sulfate was removed by filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (heptane) to obtain 0.594 g (40%) of white crystals.

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