تفاعل #1277

معادلة التفاعل

3,4-difluorobromobenzene

water

4-(4-propylcyclohexyl)-phenyltrimethoxysilane

TBAF

→

white crystals

المردود 94.5%

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

المردود 94.5%

المذيبات

toluene

toluene

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter the solvent was removed under reduced pressure
2. 2
   درجة الحرارةThe resulting mixture was refluxed for 3 hours
3. 3
   درجة الحرارةAfter cooling, to the reaction mixture
4. 4
   أخرىThe organic layer was separated
5. 5
   استخلاصthe aqueous layer was extracted with toluene three times
6. 6
   تجفيفThe combined organic layer was dried over magnesium sulfate
7. 7
   أخرىAfter the magnesium sulfate was removed by filtration
8. 8
   أخرىthe filtrate was evaporated under reduced pressure
9. 9
   أخرىThe residue was purified by silica gel column chromatography (heptane)

الإجراء التجريبي

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.

المصدر