N-bromobutanimide → 1,5-Dibromo-2,4-difluorobenzene

HRID 34012

Reaktionsgleichung

Reaktionsgleichung von HRID 34012
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[Br:10]N1C(=O)CCC1=O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([Br:10])[C:5]([F:8])=[CH:4][C:3]=1[F:9]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 676741-Bromo-2,4-difluorobenzene

Produkt 1

HCID 105645111,5-Dibromo-2,4-difluorobenzeneAusbeute 96,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

Under ice cooling, a solution of 25.35 g of 1-bromo-2,4-difluorobenzene in 100 mL of concentrated sulfuric acid was added with 25.7 g of N-bromosuccinimide, and stirred for 30 minutes at this temperature and for 2 days at room temperature. After cooling on ice, the reaction solution was added with ice, and extracted with 300 mL of diethyl ether. The organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified and separated by silica gel column chromatography (n-hexane), to afford 34.6 g of the title compound as a colorless oil.

Aufarbeitung

  1. temperatureAfter cooling on ice
  2. additionthe reaction solution was added with ice
  3. extractionextracted with 300 mL of diethyl ether
  4. washThe organic layer was successively washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting crude product was purified
  8. customseparated by silica gel column chromatography (n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-212fd29e870144d78e5e3e6f181494d7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429609B2

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