m-Chloroperbenzoic acid → HCID 53800075, compound

HRID 266494Notes

Reaction equation

HRID 266494 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[C:26]([Cl:27])=[C:25]([S:28][CH3:29])[CH:24]=[CH:23][C:14]=1[C:15]([C:17]1[CH:18]=[N:19][O:20][C:21]=1[CH3:22])=[O:16]>ClCCl>[Cl:12][C:13]1[C:26]([Cl:27])=[C:25]([S:28]([CH3:29])=[O:9])[CH:24]=[CH:23][C:14]=1[C:15]([C:17]1[CH:18]=[N:19][O:20][C:21]=1[CH3:22])=[O:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53921655HCID 53921655, compound

Product 1

HCID 53800075HCID 53800075, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

3-Chloroperbenzoic acid (85%, 0.99 g) was added portionwise to a stirred solution of 4-(2,3-dichloro-4-methylsulphenylbenzoyl)-5-methylisoxazole (1.5 g) in dichloromethane (50 ml) whilst maintaining the temperature below -20° C. The mixture was stirred at -20° C. for 1 hour. Dichloromethane (50 ml) was added and the solid was removed by filtration. The filtrate was evaporated to dryness and the residue was chromatographed on silica eluted with a mixture of ethyl acetate and cyclohexane (1:5) to give 4-(2,3-dichloro-4-methylsulphinylbenzoyl)-5-methylisoxazole (compound 46, 0.8 g) as a white solid, mp 125°-126.4° C.

Workup

  1. temperaturewhilst maintaining the temperature below -20° C
  2. customthe solid was removed by filtration
  3. customThe filtrate was evaporated to dryness
  4. customthe residue was chromatographed on silica
  5. washeluted with a mixture of ethyl acetate and cyclohexane (1:5)

Sources & evidence

ORD record
ord-24868100527a42c1a17d04abb7fc8588
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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