Potassium Hydroxide → 3-Bromo-benzofuran-5-carbaldehyde

HRID 2261094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261094
Br[CH:2]1[CH:6]([Br:7])[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3]1.[OH-].[K+]>C(O)C.O>[Br:7][C:6]1[C:5]2[CH:8]=[C:9]([CH:12]=[O:13])[CH:10]=[CH:11][C:4]=2[O:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 14797Potassium HydroxideHCID 574696642,3-Dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde

Produkt 1

HCID 574696633-Bromo-benzofuran-5-carbaldehydeAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2,3-dibromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (4.1 g) in dry ethanol (15 mL) was added a solution of KOH (2.2 eq.) in dry ethanol (14 mL) and refluxed at 70° C. for 1 h. The reaction mixture was cooled, diluted with water and extracted with EtOAc (3×50 mL). The organic layer was washed with water, brine and dried. The solvent was removed under vacuum and the residue was purified by flash chromatography (pet. ether/EtOAc 99.5:0.5) to give the title compound as a pale yellow solid (2.91 g (80% pure), yield=78%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by flash chromatography (pet. ether/EtOAc 99.5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-536903aa5f574ebc9f6f46b5770fc5cd
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846925B2

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