m-Chloroperbenzoic acid → HCID 18989182, compound

HRID 2395549Notes

Reaction equation

HRID 2395549 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([C:11]2[CH:21]=[CH:20][C:14]3[O:15][C:16]([F:19])([F:18])[O:17][C:13]=3[C:12]=2[S:22]([CH3:24])=[O:23])=[O:10])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([C:11]2[CH:21]=[CH:20][C:14]3[O:15][C:16]([F:19])([F:18])[O:17][C:13]=3[C:12]=2[S:22]([CH3:24])(=[O:33])=[O:23])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18989172HCID 18989172, compound

Product 1

HCID 18989182HCID 18989182, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-cyclopropyl-4-(2,2-difluoro-4-methylsulphinyl-1,3-benzodioxol-5-oyl)isoxazole (1.0 g) in dichloromethane was stirred with m-chloroperbenzoic acid (55%, 1.33 g) for 5 hours, then washed in turn with sodium metabisulphite solution, saturated sodium bicarbonate solution and water. The solution was dried (magnesium sulphate), evaporated to dryness and the residue recrystallised from toluene/cyclohexane to give 5-cyclopropyl-4-(2,2-difluoro-4-methylsulphonyl-1,3-benzodioxol-5-oyl)isoxazole (compound 6, 0.94 g) as a colourless solid, m.p. 162°-163° C.

Workup

  1. washwashed in turn with sodium metabisulphite solution, saturated sodium bicarbonate solution and water
  2. dry with materialThe solution was dried (magnesium sulphate)
  3. customevaporated to dryness
  4. customthe residue recrystallised from toluene/cyclohexane

Sources & evidence

ORD record
ord-679a32efc2fb45329b43348c63928c5d
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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