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

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Reaction Steps

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.

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