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m-Chloroperbenzoic acid → 4-[5-(3,5-Dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester

HRID 69401
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 69401
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14](SC)[C:13]([C:21]3[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=3)([C:17]([F:20])([F:19])[F:18])[O:12][N:11]=2)=[CH:6][C:5]=1[CH3:29].Cl[C:32]1C=C(C=CC=1)C(OO)=O.[S:42](S([O-])=O)([O-:45])(=O)=[O:43].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]([S:42]([CH3:32])(=[O:45])=[O:43])[C:13]([C:21]3[CH:22]=[C:23]([Cl:28])[CH:24]=[C:25]([Cl:27])[CH:26]=3)([C:17]([F:20])([F:19])[F:18])[O:12][N:11]=2)=[CH:6][C:5]=1[CH3:29]
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Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acid3×HCID 656671Sodium PyrosulfiteHCID 66986689HCID 66986689, Verbindung

Produkt 1

HCID 672171444-[5-(3,5-Dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4-methylsulfanyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester (428 mg) in dichloromethane (15 ml) was added 3-chloroperoxybenzoic acid (“MCPBA”) (500 mg) dropwise at ambient temperature. The reaction mixture was stirred for 5 hours then more 3-chloroperoxubenzoic acid (“MCPBA”) (300 mg) was added dropwise. The reaction mixture was allowed to stand at ambient temperature for 3 days. Then more 3-chloroperbenzoic acid (“MCPBA”) (100 mg) was added dropwise. The reaction mixture was allowed to stand at ambient temperature for another day. The reaction mixture was then treated with aqueous sodium metabisulfite (saturated) and extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: heptane/diethyl ether 6:4) to give 4-[5-(3,5-dichloro-phenyl)-4-methanesulfonyl-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester (300 mg) as white foam. 1H-NMR (CDCl3, 400 MHz): 8.01-7.52 (m, 6H), 5.28 (s, 1H), 3.91 (s, 3H), 2.65 (s, 3H), 2.47 (s, 3H) ppm.

Aufarbeitung

  1. waitto stand at ambient temperature for 3 days
  2. waitto stand at ambient temperature for another day
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (eluent: heptane/diethyl ether 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-cb4b6812d6c84ab2a9455ed7c0a09d7b
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08822502B2

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