Bromine → Ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate

HRID 395662

Reaktionsgleichung

Reaktionsgleichung von HRID 395662
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:4][CH:3]=1.[Br:23]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:23][CH:13]([C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:1])=[CH:3][CH:4]=1)=[O:22])[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Komponenten

5

Edukt 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 18174724Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate

Produkt 1

HCID 18174722Ethyl 5-bromo-6-(4-fluoro-1-naphthyl)-6-oxohexanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 6-(4-fluoro-1-naphthyl)-6-oxohexanoate (27.7 g) was dissolved in methylene chloride (100 ml), and bromine (14.6 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, which was extracted with diethyl ether (300 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-fluoro-1-naphthyl)-6-oxohexanoate as an oil (34.9 g, quantitative).

Aufarbeitung

  1. stirringAfter an hour of stirring at room temperature
  2. extractionwas extracted with diethyl ether (300 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-c740ee1753274f778be8a866628a3788
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605629B1

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