Bromine → Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoate

HRID 563103

Reaktionsgleichung

Reaktionsgleichung von HRID 563103
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:17])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1.[Br:18]Br.S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:18][CH:8]([C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:17])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Komponenten

5

Edukt 3

HCID 24408Bromine2×HCID 24437Sodium SulfiteHCID 18174688Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate

Produkt 1

HCID 18174681Ethyl 5-bromo-6-(5-chloro-2-thienyl)-6-oxohexanoateAusbeute 118,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 6-(5-chloro-2-thienyl)-6-oxohexanoate (50.0 g) was dissolved in methylene chloride (150 ml), to which was added dropwise bromine (24.5 g) with stirring at room temperature. The mixture was stirred at room temperature for 1 hour, a 10% aqueous solution of sodium sulfite was then carefully added until disappearance of the red color of bromine, which was extracted with diethyl ether (200 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-(5-chloro-2-thienyl)-6-oxohexanoate as an oil (64.4 g, >99%).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionwas extracted with diethyl ether (200 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-6aaca899621744af96f3a2ab3e9050ca
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067453B2

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