Reaction #933

Reaction equation

m-chloroperbenzoic acid

sodium bisulfite

water

2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile

2-Fluoro-6-[(3 -methoxyphenyl)thio]benzonitrile

m-chloroperbenzoic acid

→

2-Fluoro-6-[(3 -methoxyphenyl)sulfonyl]benzonitrile

Conditions

Workup

1. 1
   ExtractionThe H2O solution was extracted with EtOAc
2. 2
   DryingAfter drying over MgSO4 and solvent removal
3. 3
   Otherthe resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the fluent
4. 4
   OtherThis resulted in 1.15 g of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid

Procedure

To a solution of 2 g (7.7 mmol) of 2-fluoro-6-[(3-methoxyphenyl)thio]benzonitrile (Example 13) was added 2.93 g (17 mmol) of m-chloroperbenzoic acid. The resultant mixture was stirred for 24 h. Additional 0.29 g of m-chloroperbenzoic acid was added and the resultant mixture was stirred for 15 min. Excess sodium bisulfite was added, followed by water. The H2O solution was extracted with EtOAc. After drying over MgSO4 and solvent removal, the resultant crude product was purified by flash column chromatography on silica gel with methylene chloride as the fluent. This resulted in 1.15 g of 2-fluoro-6-[(3-methoxyphenyl)sulfonyl]benzonitrile as a solid: mp 113°-117° C.

Source