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

HRID 21446Notes

Reaction equation

HRID 21446 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-chloro-4-(methylsulphenyl)phenyl]-4-cyclopropylcarbonyl-isoxazole (1.0g) 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 flitrate was evaporated to dryness to give 4-cyclopropylcarbonyl-5-[3-chloro-4-(methylsulphonyl)phenyl]isoxazole (compound 5, 1.11g) 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 flitrate was evaporated to dryness

Sources & evidence

ORD record
ord-e02f35406a32485781b112d02580c207
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Reaction notes

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