Reaktion #938

Reaktionsgleichung

water

OXONE

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

OXONE

→

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

Ausbeute 65.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring 1 h
2. 2
   workup.STIRRINGThe reaction was stirred for 18 h
3. 3
   SonstigeThe solid was removed by vacuum filtration
4. 4
   Waschenwashed with 200 ml of methanol
5. 5
   EinengenThe filtrate was concentrated to dryness
6. 6
   Sonstigechromatographed on silica gel (flash; Hex/EtOAc 1:1)

Vorschrift

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. (5.26 g, 8.6 mmol) in 30 ml of water was added dropwise with stirring. After stirring 1 h, another 1.5 equivalents of OXONE® (3.60 g 5.9 mmol) was added. The reaction was stirred for 18 h. The solid was removed by vacuum filtration and washed with 200 ml of methanol, then with 2×60 ml of acetone. The filtrate was concentrated to dryness and chromatographed on silica gel (flash; Hex/EtOAc 1:1) to provide 0.73 g (65%) of 2-[(3,5-dimethylphenyl)sulfonyl]-6-fluorobenzonitrile: mp 167°-168° C.

Quelle