Reaction #586143

Reaction equation

2-methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile

( b )

2-methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile

→

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

Yield 51.0%

Solvents

trifluoroacetic anhydride

Conditions

Workup

1. 1
   workup.DISTILLATIONthe low-boiling matters were distilled off under reduced pressure
2. 2
   workup.ADDITION50 ml of methanol and 3 g of 20% aqueous potassium hydroxide were added to the residue
3. 3
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
4. 4
   workup.ADDITIONthe residue was mixed with 5% aqueous sulfuric acid
5. 5
   Extractionextracted with ethyl acetate
6. 6
   DryingThe ethyl acetate layer was dried over anhydrous sodium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Procedure

2.2 g (7.1 mmol) of 2-methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile prepared in (b) was stirred in 15 ml of trifluoroacetic anhydride at room temperature for 12 hours, and the low-boiling matters were distilled off under reduced pressure. 50 ml of methanol and 3 g of 20% aqueous potassium hydroxide were added to the residue, and the reaction was carried out for 1 hour. The solvent was distilled off under reduced pressure, and the residue was mixed with 5% aqueous sulfuric acid and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.0 g of 2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile (yield 51.0%), which was used in Example 1 as the starting material.

Source