反応 #53562

反応方程式

4-trifluoromethylphenyl boronic acid

3-bromophenyl cyclopentyl sulfide

sodium carbonate

toluene

→

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

収率 78.0%

溶媒

water

ethanol

反応条件

後処理

1. 1
   温度refluxed
2. 2
   温度under heating
3. 3
   その他The resulting reaction mixture
4. 4
   workup.ADDITIONwas poured into ice-cold water
5. 5
   抽出extracted with toluene
6. 6
   洗浄The toluene layer was washed with water twice
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   その他Purification of the residue by silica gel column chromatography

実験手順

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).

出典