Reaction #586142

Reaction equation

2-fluoro-4-(4-trifluoromethylphenyl)benzonitrile

sodium methyl mercaptan

→

2-methylthio-4-(4-trifluoromethylphenyl)benzonitrile

Yield 75.4%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with 100 ml of ethyl acetate twice
2. 2
   WashThe ethyl acetate layer was washed with 100 ml of water twice
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
5. 5
   OtherPurification of the residue by silica gel column chromatography

Procedure

To 3.0 g (11.3 mmol) of 2-fluoro-4-(4-trifluoromethylphenyl)benzonitrile in 50 ml of N,N-dimethylformamide, 7.0 g (15.0 mmol) of 15% aqueous sodium methyl mercaptan was added dropwise at room temperature. After 6 hours of stirring at 60° C., the reaction mixture was poured into 200 ml of ice-cold water and extracted with 100 ml of ethyl acetate twice. The ethyl acetate layer was washed with 100 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 2.5 g of 2-methylthio-4-(4-trifluoromethylphenyl)benzonitrile (yield 75%) as white crystals (m.p. 128-129° C.).

Source