Sodium Hydroxide → 2,7-Dibromo-9-(2-ethylhexyl)carbazole

HRID 2244960

Reaktionsgleichung

Reaktionsgleichung von HRID 2244960
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.Br[CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22].S.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>CC(C)=O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[N:5]([CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromideHCID 111515032,7-DibromocarbazoleHCID 162054371-Butanaminium,N,N,N-tributyl-, sulfide (1:1)

Produkt 1

HCID 120705112,7-Dibromo-9-(2-ethylhexyl)carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2,7-dibromocarbazole (3.0 g, 8.95 mmol), 1-bromo-2-ethylhexane (2.70 g, 13.4 mmol), tetra-n-butylammonium hydrogen sulfide (0.1 g), and NaOH (0.54 g, 13.5 mmol) in acetone (30 mL) was refluxed for 9 h. After the reaction, the acetone was removed under vacuum and the residue was extracted with toluene. The combined organic layer was washed with a saturated NaCl aqueous solution, and dried over MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel using hexane as the eluent to afford 2,7-dibromo-9-(2-ethylhexyl)-carbazole as a white powder. Yield: 2.46 g (62.9%). M.P.: 95-97° C.

Aufarbeitung

  1. temperaturewas refluxed for 9 h
  2. customAfter the reaction
  3. customthe acetone was removed under vacuum
  4. extractionthe residue was extracted with toluene
  5. washThe combined organic layer was washed with a saturated NaCl aqueous solution
  6. dry with materialdried over MgSO4
  7. customAfter removal of the solvent
  8. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-4b20a7e3c8ab4988ba23464f0cb0a5ff
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07679082B2

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