반응 #1277

반응 방정식

3,4-difluorobromobenzene

water

4-(4-propylcyclohexyl)-phenyltrimethoxysilane

TBAF

→

white crystals

수율 94.5%

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

수율 94.5%

용매

toluene

toluene

toluene

반응 조건

후처리

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

실험 절차

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.

출처