Bromine → Ethyl 5-bromo-6-(4-fluorophenyl)-6-oxohexanoate

HRID 747452

Reaktionsgleichung

Reaktionsgleichung von HRID 747452
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.[Br:19]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:19][CH:9]([C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

5

Edukt 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 18174682Ethyl-6-(4-fluorophenyl)-6-oxohexanoate

Produkt 1

HCID 18174689Ethyl 5-bromo-6-(4-fluorophenyl)-6-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 6-(4-fluorophenyl)-6-oxohexanoate (14.0 g) was dissolved in methylene chloride (100 ml), and bromine (8.87 g) was added dropwise with stirring at room temperature. After an hour of stirring at room temperature, a 10% aqueous solution of sodium sulfite was carefully added until disappearance of the red color of bromine, and the mixture was then extracted with diethyl ether (100 ml×2). The organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml), dried over anhydrous magnesium sulfate, and concentrated to give ethyl 5-bromo-6-(4-fluorophenyl)-6-oxohexanoate as an oil (17.6 g, quantitative).

Aufarbeitung

  1. stirringAfter an hour of stirring at room temperature
  2. extractionthe mixture was then extracted with diethyl ether (100 ml×2)
  3. washThe organic layer was washed with a 10% aqueous solution of sodium hydrogen carbonate (100 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-685027c1db874bd1b233e5d715c9471a
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396848B1

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