Reaction #586130

Reaction equation

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

sodium hydride

ethanethiol

hydrogen

→

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

Yield 88.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONwas added
3. 3
   Extractionextracted with 50 ml of ethyl acetate twice
4. 4
   WashThe ethyl acetate layer was washed with 50 ml of water twice
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
7. 7
   OtherPurification of the residue by silica gel column chromatography

Procedure

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.).

Source