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

HRID 2244960

Reaction equation

HRID 2244960 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4b20a7e3c8ab4988ba23464f0cb0a5ff
Source dataset
uspto-grants-2010_03
Patent number
US07679082B2

Linked notes

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