Carbazole → 9-Decyl-9H-carbazole

HRID 2285336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2285336
[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[CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH-].[Na+]>[Br+].C([N+](CCCC)(CCCC)CCCC)CCC.C1C=CC=CC=1>[CH2:15]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Komponenten

6

Edukt 3

HCID 6854CarbazoleHCID 81731-BromodecaneHCID 14798Sodium Hydroxide

Produkt 1

HCID 123386259-Decyl-9H-carbazoleAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178449040HCID 178449040, VerbindungKatalysatorHCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of carbazole (2.1 g, 12.5 mmol), benzene (10 mL), tetrabutylammonium bromine (0.1 g, 0.7 mmol) and 1-bromodecane (3.0 mL, 15 mmol), was added 50% NaOH aqueous solution (15 mL). The solution mixture was heated to 80° C. and stirred for 2 h. The solvent was evaporated in vacuo and the residue was extracted with dichloromethane (3×30 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of solvent, the product was purified by silica gel column chromatography using petroleum ether/dichloromethane as eluent affording 9-decylcarbazole as a colorless liquid (3.4 g, 90%). 1H NMR (400 MHz, CDCl3, δ) 8.10 (d, J=7.6 Hz, 2H), 7.48-7.38 (m, 4H), 7.24 (dd, J=14.4 Hz, J=1.2 Hz, 2H), 4.30 (t, J=7.2 Hz, 2H), 1.89-1.81 (m, 2H), 1.39-1.23 (m, 14H), 0.88 (t, J=7.0 Hz, 3H). 13C NMR (100 MHz, CDCl3, δ) 140.4, 125.5, 122.8, 120.3, 118.6, 108.6, 43.1, 31.8, 29.5, 29.48, 29.40, 29.3, 28.9, 27.3, 22.7, 14.1. MS (MALDI-TOF): m/z 307.2579 (M+).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. extractionthe residue was extracted with dichloromethane (3×30 mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customAfter removal of solvent
  6. customthe product was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c980790e19bd4b7dba3d2df665551ca7
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09147848B2

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