m-Chloroperbenzoic acid → HCID 18953292, compound

HRID 1491571Notes

Reaction equation

HRID 1491571 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9](=[O:28])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[S:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:34]>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9](=[O:28])[C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[S:20]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[O:34])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18953312HCID 18953312, compound

Product 1

HCID 18953292HCID 18953292, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-12 °C

Procedure

A mixture of 5-cyclopropyl-4-[2-(4-chlorophenylsulphenyl)-4-trifluoromethylbenzoyl]isoxazole (1.14 g) and 3-chloroperoxybenzoic acid (0.84 g) in dichloromethane was stirred at -12° C. for 15 minutes. The precipitate was filtered and the filtrate was washed with aqueous sodium metabisulphite, aqueous sodium bicarbonate and a solution of brine and ammonium chloride, dried over anhydrous sodium sulphate and filtered. The dichloromethane was evaporated and the residue was crystallised from ethanol to give 5-cyclopropyl-4-[2-(4-chlorophenylsulphinyl)-4-trifluoromethylbenzoyl]isoxazole (compound 9, 0.86 g) as white crystals, m.p. 151° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washthe filtrate was washed with aqueous sodium metabisulphite, aqueous sodium bicarbonate
  3. dry with materiala solution of brine and ammonium chloride, dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customThe dichloromethane was evaporated
  6. customthe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-558febd92a41419cbe4c5ea840b19856
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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