Iodoethane → Ethyl 3-bromofuran-2-carboxylate

HRID 1361899

Reaktionsgleichung

Reaktionsgleichung von HRID 1361899
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].[CH2:10](I)[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 6054793-Bromofuran-2-carboxylic acid

Produkt 1

HCID 22456149Ethyl 3-bromofuran-2-carboxylateAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3-Bromofuran-2-carboxylic acid (1.86 g, 9.75 mmol), ethyl iodide (3.1 mL, 38.8 mol) and cesium carbonate (4.80 g, 14.7 mmol) were suspended in acetonitrile (50 mL), followed by stirring at 80° C. for 3 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1) to afford ethyl 3-bromofuran-2-carboxylate (1.16 g, 54%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d5bfc4c465ad4b3bbd3874a6474ffd1b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880013B2

Verknüpfte Notizen

Wird geladen…