反応 #1277

反応方程式

3,4-difluorobromobenzene

water

4-(4-propylcyclohexyl)-phenyltrimethoxysilane

TBAF

→

white crystals

収率 94.5%

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

収率 94.5%

溶媒

toluene

toluene

toluene

反応条件

後処理

1. 1
   その他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
   その他The organic layer was separated
5. 5
   抽出the aqueous layer was extracted with toluene three times
6. 6
   乾燥The combined organic layer was dried over magnesium sulfate
7. 7
   その他After the magnesium sulfate was removed by filtration
8. 8
   その他the filtrate was evaporated under reduced pressure
9. 9
   その他The residue was purified by silica gel column chromatography (heptane)

実験手順

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.

出典