Potassium Carbonate → (9H-Carbazol-4-yloxy)acetonitrile

HRID 1057651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057651
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([OH:14])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]#[N:24]>C(#N)C>[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4]([O:14][CH2:22][C:23]#[N:24])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 1042514-Hydroxycarbazole

Produkt 1

HCID 18671668(9H-Carbazol-4-yloxy)acetonitrileAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 9H-carbazol-4-ol (1.1 g, 6.0 mmol) in acetonitrile (100 mL) is added potassium carbonate (1.66 g, 12 mmol) and bromoacetonitrile (0.42 mL, 6.0 mmol). The mixture is stirred at room temperature for 20 h. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography, silica gel (100 mL), using CH2Cl2 as eluent gave 1.13 g (85%) of the title compound; 1H NMR (DMSO-d6) δ5.4, 6.81, 7.18, 7.36, 7.46, 8.09; Anal. Calcd for C14H10N2O: C, 75.66; H, 4.53; N, 12.60. Found: C, 75.18; H, 4.56; N, 12.54.

Aufarbeitung

  1. customThe mixture is partitioned between water and CH2Cl2
  2. customThe layers are separated
  3. dry with materialthe organic layer dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-87edf34fdb684b83892f85548bb67d73
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514968B1

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