Réaction #53562

Équation de réaction

4-trifluoromethylphenyl boronic acid

3-bromophenyl cyclopentyl sulfide

sodium carbonate

toluene

→

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

Rendement 78.0%

Solvants

water

ethanol

Conditions de réaction

Traitement

1. 1
   Températurerefluxed
2. 2
   Températureunder heating
3. 3
   AutreThe resulting reaction mixture
4. 4
   workup.ADDITIONwas poured into ice-cold water
5. 5
   Extractionextracted with toluene
6. 6
   LavageThe toluene layer was washed with water twice
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   AutrePurification of the residue by silica gel column chromatography

Mode opératoire

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).

Source