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

HRID 47652Notes

Reaction equation

HRID 47652 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 99244894-[3,5-Difluoro-4-(methylsulfonyl)-phenyl]-5-methyl-3-phenylisoxazoleYield 93.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7cbd6652612f4c55b07a8147385f28b2
Source dataset
uspto-grants-2004_03
Patent number
US06699884B2

Reaction notes

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