反応 #53555

反応方程式

water

2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile

potassium tert-butoxide

→

2-(2-propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile

収率 43.5%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   抽出extracted with 50 ml of ethyl acetate twice
3. 3
   洗浄The ethyl acetate layer was washed with 50 ml of water twice
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
6. 6
   その他Purification of the residue by silica gel column chromatography

実験手順

1.0 g (3.6 mmol) of 2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile, 0.45 g (4.0 mmol) of potassium tert-butoxide and 0.5 g (4.1 mmol) of 3-propenyl bromide were stirred in 20 ml of N,N-dimethylformamide at room temperature for 1 hour. The resulting reaction mixture was poured into 20 ml of water and extracted with 50 ml of ethyl acetate twice. The ethyl acetate layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.5 g of 2-(2-propenylthio)-4-(4-trifluoromethylphenyl)benzonitrile (yield 43.0%) as yellow crystals (m.p. 89-90° C.).

出典