m-Chloroperbenzoic acid → HCID 10981874, compound

HRID 1492382Notes

Reaction equation

HRID 1492382 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[N:10][O:11][C:12]=2[CH:13]2[CH2:15][CH2:14]2)=[O:7])=[C:4]([CH2:18]SC)[CH:3]=1.Cl[C:22]1C=CC=C(C(OO)=O)C=1.[S:32](=[O:35])(O)[O-:33].[Na+]>ClCCl>[CH:13]1([C:12]2[O:11][N:10]=[CH:9][C:8]=2[C:6](=[O:7])[C:5]2[CH:16]=[CH:17][C:2]([Br:1])=[CH:3][C:4]=2[CH2:18][S:32]([CH3:22])(=[O:35])=[O:33])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 18950277HCID 18950277, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 10981874HCID 10981874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-[4-bromo-2-(methylsulphenylmethyl)benzoyl]-5-cyclopropylisoxazole (0.7 g) and 3-chloroperbenzoic acid (1.5 g) in dichloromethane was stirred for 30 minutes at 0° C. and then at 1 hour at 25° C. The mixture was then treated with an aqueous solution of sodium bisulphite and filtered. After decanting, the organic layer was washed with a solution of sodium acetate, brine, dried (sodium sulphate), filtered and evaporated to yield a clean oil which was crystallised from ether to give 5-cyclopropyl-4-[4-bromo-2-(methylsulphonylmethyl)benzoyl]isoxazole (compound 2, 0.61 g) as a white solid, m.p. 154.2° C.

Workup

  1. waitat 1 hour at 25° C
  2. filtrationfiltered
  3. customAfter decanting
  4. washthe organic layer was washed with a solution of sodium acetate, brine
  5. dry with materialdried (sodium sulphate)
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a clean oil which
  9. customwas crystallised from ether

Sources & evidence

ORD record
ord-ae3faa7b79fd4009b6ca072f6a569724
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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