Reaction #937

Reaction equation

2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile

OXONE

→

2-[(3,5-dimethylphenyl)sulfinyl]-6-fluorobenzonitrile

Yield 47.0%

Solvents

water

methanol

Conditions

Workup

1. 1
   workup.STIRRINGAfter stirring 1.5 h
2. 2
   Otherthe solid was removed by vacuum filtration
3. 3
   Washwashed with 3×50 ml of methanol
4. 4
   ConcentrationThe filtrate was concentrated to dryness
5. 5
   Otherchromatographed on silica
6. 6
   Otherget (flash; Hex/EtOAc 2:1)

Procedure

2-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrile (Example 18) (1.0 g, 3.9 mmol) was dissolved in 100 ml of methanol. A solution of OXONE®.dagger. (2.63 g, 4.3 mmol) in 15 ml of water was added dropwise with stirring. After stirring 1.5 h, the solid was removed by vacuum filtration and washed with 3×50 ml of methanol. The filtrate was concentrated to dryness and chromatographed on silica get (flash; Hex/EtOAc 2:1) to provide 0.5 g (47%) of 2-[(3,5-dimethylphenyl)sulfinyl]-6-fluorobenzonitrile: mp 146°-147° C.

Source