Water → 3,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole

HRID 2244959Notes

Reaction equation

HRID 2244959 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28].O>CN(C=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:23][CH:24]([CH2:29][CH3:30])[CH2:25][CH2:26][CH2:27][CH3:28])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 868042-Ethylhexyl bromideHCID 2748743,6-Dibromocarbazole

Product 1

HCID 167529093,6-Dibromo-9-(2-ethylhexyl)-9H-carbazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,6-dibromocarbazole (3.0 g, 8.95 mmol) in 25 mL of dried DMF was added potassium carbonate (2.47 g, 17.9 mmol). The mixture was stirred and degassed for 1 h, after which 1-bromo-2-ethylhexane (2.70 g, 13.4 mmol) was added dropwise, followed by refluxing for 2 days. The reaction mixture was poured into 100 mL of distilled water and extracted with chloroform. The combined organic layer was dried with anhydrous magnesium sulfate. After removal of the solvent and unreacted 2-ethylhexyl bromide under reduced pressure, the residue was purified by column chromatography on silica gel using hexane and ethyl acetate as the eluent to afford 3,6-dibromo-9-(2-ethylhexyl)-carbazole as a waxy solid. Yield: 3.02 g (77.2%), M.P.: 62.4-63.6° C.

Workup

  1. customdegassed for 1 h
  2. temperatureby refluxing for 2 days
  3. extractionextracted with chloroform
  4. dry with materialThe combined organic layer was dried with anhydrous magnesium sulfate
  5. customAfter removal of the solvent and unreacted 2-ethylhexyl bromide under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9195a3e60fc94856a8876026435b5b5b
Source dataset
uspto-grants-2010_03
Patent number
US07679082B2

Reaction notes

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