反応 #586130

反応方程式

2-fluoro-4-(2,4-dichlorophenyl)benzonitrile

sodium hydride

ethanethiol

hydrogen

→

4-(2,4-dichlorophenyl)-2-ethylthiobenzonitrile

収率 88.0%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONwas added
3. 3
   抽出extracted with 50 ml of ethyl acetate twice
4. 4
   洗浄The ethyl acetate layer was washed with 50 ml of water twice
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
7. 7
   その他Purification of the residue by silica gel column chromatography

実験手順

0.12 g (3.0 mmol) of 60% sodium hydride was stirred in 30 ml of N,N-dimethylformamide at room temperature while 0.2 g (3.2 mmol) of ethanethiol was added dropwise. After generation of hydrogen was over, 0.7 g (2.6 mmol) of 2-fluoro-4-(2,4-dichlorophenyl)benzonitrile was added, and the reaction mixture was stirred at 60° C. for 6 hours. The reaction mixture was poured into about 100 ml of ice-cold 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 0.7 g of 4-(2,4-dichlorophenyl)-2-ethylthiobenzonitrile (yield 88.0%) as pale yellow crystals (m.p. 89-92° C.).

出典