반응 #53562

반응 방정식

4-trifluoromethylphenyl boronic acid

3-bromophenyl cyclopentyl sulfide

sodium carbonate

toluene

→

[3-(4-trifluoromethylphenyl)phenyl] cyclopentyl sulfide

수율 78.0%

용매

water

ethanol

반응 조건

후처리

1. 1
   온도refluxed
2. 2
   온도under heating
3. 3
   기타The resulting reaction mixture
4. 4
   workup.ADDITIONwas poured into ice-cold water
5. 5
   추출extracted with toluene
6. 6
   세척The toluene layer was washed with water twice
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   기타Purification of the residue by silica gel column chromatography

실험 절차

1.0 g (5.2 mol) of 4-trifluoromethylphenyl boronic acid, 1.4 g (5.4 mmol) of 3-bromophenyl cyclopentyl sulfide, 1.6 g (15.0 mmol) of sodium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 50 ml of toluene, 25 ml of ethanol and 25 ml of water and refluxed under heating and stirring for 2 hours. The resulting reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.3 g of [3-(4-trifluoromethylphenyl)phenyl] cyclopentyl sulfide (yield 78.0%) as a colorless liquid (nD20 1.5732).

출처