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

HRID 841

Reaction equation

HRID 841 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[OH:19]OS([O-])=O.[K+]>CO.O>[CH3:8][C:6]1[CH:5]=[C:4]([S:9]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=[O:19])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

5

Reactant 2

HCID 108487512-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrileHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 107309642-[(3,5-Dimethylphenyl)sulfinyl]-6-fluorobenzonitrileYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

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.

Workup

  1. stirringAfter stirring 1.5 h
  2. customthe solid was removed by vacuum filtration
  3. washwashed with 3×50 ml of methanol
  4. concentrationThe filtrate was concentrated to dryness
  5. customchromatographed on silica
  6. customget (flash; Hex/EtOAc 2:1)

Sources & evidence

ORD record
ord-6ddfb59c25f34fe781aa3d4f78fc3efa
Source dataset
uspto-grants-1998_03
Patent number
US05723452

Linked notes

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