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Sulfuric Acid → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acid

HRID 1096099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1096099
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:26])([F:25])[F:24])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[C:16]([F:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cr](O)(O)(=O)=[O:28].S(=O)(=O)(O)O>CC(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:23]([F:25])([F:24])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([OH:28])=[O:21])=[C:16]([F:22])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 231598185-(3,5-Dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Produkt 1

HCID 866114634-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-fluoro benzoic acidAusbeute 68,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180
Acetone
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

In a solution of 0.95 g of 5-(3,5-dichlorophenyl)-3-(3-fluoro-4-hydroxymethylphenyl)-5-trifluoromethyl-4,5-dihy droisoxazole in 25 ml of acetone, Johnes' Reagent prepared from 1.50 g of chromic acid, 1.2 ml of concentrated sulfuric acid and 7 ml of water was added dropwise under cooling with ice and with stirring, after the completion of the addition dropwise, continued to stir at room temperature for further 1.5 hour. After the completion of the reaction, the reaction mixture was poured in 50 ml of water and extracted with diethyl ether (50 ml×1). The organic phase was dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 0.67 g of the aimed product as beige crystal.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureunder cooling with ice
  3. additionafter the completion of the addition dropwise
  4. stirringto stir at room temperature for further 1.5 hour
  5. customAfter the completion of the reaction
  6. extractionextracted with diethyl ether (50 ml×1)
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. washThe residual solid was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-55861b336e464d1b8ed3b89175b7c3d5
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08138213B2

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