تفاعل #53562

معادلة التفاعل

4-trifluoromethylphenyl boronic acid

3-bromophenyl cyclopentyl sulfide

sodium carbonate

toluene

→

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

المردود 78.0%

المذيبات

water

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed
2. 2
   درجة الحرارةunder heating
3. 3
   أخرىThe resulting reaction mixture
4. 4
   workup.ADDITIONwas poured into ice-cold water
5. 5
   استخلاصextracted with toluene
6. 6
   غسيلThe toluene layer was washed with water twice
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   أخرىPurification of the residue by silica gel column chromatography

الإجراء التجريبي

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).

المصدر