Water → 2-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzenecarbonitrile

HRID 842

Reaktionsgleichung

Reaktionsgleichung von HRID 842
[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+].[OH2:25]>CO>[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])=[O:25])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 108487512-[(3,5-Dimethylphenyl)thio]-6-fluorobenzonitrileHCID 23707502Potassium hydroxy sulfite2×

Produkt 1

HCID 4863572-[(3,5-Dimethylphenyl)sulfonyl]-6-fluorobenzenecarbonitrileAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringAfter stirring 1 h
  2. stirringThe reaction was stirred for 18 h
  3. customThe solid was removed by vacuum filtration
  4. washwashed with 200 ml of methanol
  5. concentrationThe filtrate was concentrated to dryness
  6. customchromatographed on silica gel (flash; Hex/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a63765ce57f4be88697886cd8f75569
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723452

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