Triphenylphosphine → 9H-carbazole-4-carbaldehyde

HRID 659655Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659655
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([CH:16]=[O:17])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClC1C=CC=CC=1Cl>[CH:5]1[C:4]2[NH:1][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]=2[C:8]([CH:16]=[O:17])=[CH:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 11776TriphenylphosphineHCID 541378936-Nitrobiphenyl-2-carbaldehyde

Produkt 1

HCID 200308319H-carbazole-4-carbaldehydeAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Versuchsvorschrift

A 100-mL round-bottom flask was placed a solution of 6-nitrobiphenyl-2-carbaldehyde (6.2 g, 27.31 mmol, 1.00 equiv) in 1,2-dichlorobenzene (60 mL). To the mixture was added PPh3 (17.9 g, 68.32 mmol, 2.50 equiv) and the mixture was heated to reflux for 30 hours. Upon completion, the resulting mixture was concentrated on a rotary evaporator to give a residue that was purified by silica gel column chromatography affording 9H-carbazole-4-carbaldehyde as yellow solid (3 g, 56%).

Aufarbeitung

  1. customA 100-mL round-bottom flask was placed
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 hours
  4. concentrationUpon completion, the resulting mixture was concentrated on a rotary evaporator
  5. customto give a residue that
  6. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d633bdda07084425ae5b2cbab783e3e4
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080566B1

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