m-Chloroperbenzoic acid → 4-Cyclopropylcarbonyl-5-[3-chloro-4-(methylsulphonyl)phenyl]isoxazole

HRID 2380193Notes

Reaction equation

HRID 2380193 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:14][N:13]=[CH:12][C:11]=2[C:15]([CH:17]2[CH2:19][CH2:18]2)=[O:16])[CH:5]=[CH:6][C:7]=1SC.Cl[C:21]1C=C(C=CC=1)C(OO)=O.[S:31](=[O:34])(O)[O-:32].[Na+]>ClCCl>[CH:17]1([C:15]([C:11]2[CH:12]=[N:13][O:14][C:10]=2[C:4]2[CH:5]=[CH:6][C:7]([S:31]([CH3:21])(=[O:34])=[O:32])=[C:2]([Cl:1])[CH:3]=2)=[O:16])[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 199317645-[3-Chloro4-(methylsulphenyl)phenyl]4-cyclopropylcarbonyl-isoxazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 199317864-Cyclopropylcarbonyl-5-[3-chloro-4-(methylsulphonyl)phenyl]isoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-[3-chloro4-(methylsulphenyl)phenyl]4-cyclopropylcarbonyl-isoxazole (1.0 g) and 3-chloroperoxybenzoic acid (2.3g, 50%) in dichloromethane was stirred overnight. A saturated solution of sodium bisulphite was added and the layers were separated. The organic phase was washed with sodium bicarbonate solution, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 4-cyclopropylcarbonyl-5-[3-chloro-4-(methylsulphonyl)phenyl]isoxazole (compound 5, 1.11 g) as a white solid, m.p. 148°-150° C.

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with sodium bicarbonate solution, water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-8d1c65b11b45491d9d1503ad98a39c12
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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