7-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde → 5-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

HRID 15174

Reaktionsgleichung

Reaktionsgleichung von HRID 15174
Br[C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[Cu][C:14]#[N:15]>CC(N(C)C)=O>[CH:11]([C:4]1[CH:3]=[C:2]([C:14]#[N:15])[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)=[O:12]

Komponenten

4

Edukt 2

HCID 185261827-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehydeHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 574869025-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrileAusbeute 61,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 h, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 18 h
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed well with warm ethyl acetate
  4. concentrationThe combined ethyl acetate layer were concentrated
  5. customdried
  6. customThe crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-5cffa760ea3a42c59d941a8a79d59029
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732460B2

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