Potassium peroxymonosulphate → 4-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazole

HRID 1838509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1838509
S([O-])(O[O-])(=O)=[O:2].[K+].[K+].[F:9][C:10]1[CH:11]=[C:12]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:13]=[C:14]([F:19])[C:15]=1[S:16]([CH3:18])=[O:17].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>O.CO.ClCCl>[F:19][C:14]1[CH:13]=[C:12]([C:20]2[C:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:22][O:23][C:24]=2[CH3:25])[CH:11]=[C:10]([F:9])[C:15]=1[S:16]([CH3:18])(=[O:2])=[O:17]

Komponenten

7

Edukt 3

HCID 10313463Potassium peroxymonosulphate2×HCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 227456134-[3,5-Difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole

Produkt 1

HCID 99244894-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazoleAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Potassium peroxymonosulfate (0.25 g, 0.40 mmol) and water (7 mL) were added to a mixture of 4-[3,5-difluoro-4-(methyl-sulfinyl)phenyl]-5-methyl-3-phenylisoxazole (0.10 g, 0.30 mmol), dichloromethane (4 mL), and methanol (4 mL). The mixture was stirred for four days at room temperature. To the mixture was added magnesium monoperoxyphathalate hexahydrate (0.50 g, 0.80 mmol), dichloromethane (20 mL), methanol (10 mL). The mixture was stirred vigorously for 18 hours. To the mixture was added potassium peroxymonosulfate (0.35 g, 0.57 mmol), and the reaction continued for 18 hours. The mixture was poured into water and extracted with dichloromethane (4×75 mL). The combined extracts were dried with magnesium sulfate, concentrated, and the residue purified by silica gel chromatography using 30% ethyl acetate in hexanes. A white solid (98 mg, 93%) was obtained. MP 140.4-143.4° C. 1H NMR (CDCl3/400 MHz) 7.35-7.45 (m, 5H), 6.84 (d, 2H, J=9.4), 3.32 (s, 3H) 2.52 (s, 3H). ESHRMS m/z 350.0642 (M+H+, Calcd 350.0662).

Aufarbeitung

  1. stirringThe mixture was stirred vigorously for 18 hours
  2. waitthe reaction continued for 18 hours
  3. extractionextracted with dichloromethane (4×75 mL)
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ccb8b5256d64cf58457e0492844e8a5
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06673818B2

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