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

HRID 885826
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 885826
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[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:9]1[CH:10]=[C:5]([C:3](=[O:4])[C:2]([F:15])([F:16])[F:1])[CH:6]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen 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)acetophenoneAusbeute 163,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a stirred solution of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanone (5.00 g) in glacial acetic acid (1.0 mL) and concentrated sulfuric acid (6.0 mL) at 0° C. was added 1,3-dibromo-5,5-dimethylhydantoin (3.54 g). After stirring at 35° C. for 3.5 hours, the reaction mixture was poured into ice-water (60 mL) and extracted with chloroform (30 mL×2). The organic extracts were combined, washed with saturated aqueous sodium hydrogencarbonate solution (50 mL×1) and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in hexane (20 mL) and filtered, and the filtrate was concentrated under reduced pressure to provide the title compound as a yellow oil (6.50 g).

Aufarbeitung

  1. extractionextracted with chloroform (30 mL×2)
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution (50 mL×1) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in hexane (20 mL)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2473edd578834b5c8be3aa82ee8b6739
Quelldatensatz
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08242283B2

Notizen zur Reaktion

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