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1,3-Dibromo-5,5-dimethylhydantoin → 3'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone

HRID 1880245
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1880245
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][CH:6]=1)=[O:4].[Br:17]N1C(C)(C)C(=O)N(Br)C1=O>C(O)(=O)C.S(=O)(=O)(O)O>[Br:17][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone

Produkt 1

HCID 716518093'-Bromo-2,2,2-trifluoro-5'-(trifluoromethyl)acetophenone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of 5.00 g of 2,2,2-trifluoro-5′-(trifluoromethyl)acetophenone in 1 mL of acetic acid and 6 mL of concentrated sulfuric acid, 3.54 g of 1,3-dibromo-5,5-dimethylhydantoin was added and the resultant mixture was stirred at 35° C. for 3.5 hours. After the completion of the reaction, the reaction mixture was charged into 60 mL of ice water and the resultant mixture was extracted with chloroform (30 mL×2). The organic phase was washed with a saturated sodium hydrogen carbonate aqueous solution (50 mL×1) and then dehydrated and dried over saturated saline and anhydrous magnesium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 20 mL of hexane and an insoluble substance was filtered off, followed by distilling off the solvent under reduced pressure to obtain 6.50 g of the objective substance as a yellow oily substance. This substance was used in the next process as it was without being further purified.

Aufarbeitung

  1. customAfter the completion of the reaction
  2. extractionthe resultant mixture was extracted with chloroform (30 mL×2)
  3. washThe organic phase was washed with a saturated sodium hydrogen carbonate aqueous solution (50 mL×1)
  4. dry with materialdried over saturated saline and anhydrous magnesium sulfate in this order
  5. distillationthe solvent was distilled off under reduced pressure
  6. dissolutionThe resultant residue was dissolved in 20 mL of hexane
  7. filtrationan insoluble substance was filtered off
  8. distillationby distilling off the solvent under reduced pressure
  9. customto obtain 6.50 g of the objective substance as a yellow oily substance

Quellen und Nachweise

ORD-Eintrag
ord-7ae79283344f43728c40686a71797fc8
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318757B2

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