Carbazole → 9-(2-Bromophenyl)-9H-carbazole

HRID 923701

Reaction equation

HRID 923701 reaction equation
[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:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1I.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.C1(C)C(C)=CC=CC=1>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[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

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 114151-Bromo-2-iodobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 594650129-(2-Bromophenyl)-9H-carbazole

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 7237O-XyleneSolvent

Procedure

1.672 g of carbazole, 1.6 mL of 1-bromo-2-iodobenzene, 2.7646 g of potassium carbonate, 95 mg of copper iodide and 25 mL of xylene were refluxed in a nitrogen atmosphere. The mixture was cooled to room temperature, extracted with ethyl acetate, and dried with anhydrous magnesium sulfate to remove moisture, and the solvent was removed under reduced pressure. Silica gel column separation using a hexane solvent was conducted, thus obtaining a compound from which the solvent was then removed under reduced pressure, followed by vacuum drying, yielding 9-(2-bromophenyl)-9H-carbazole as a desired white solid intermediate.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customto remove moisture
  4. customthe solvent was removed under reduced pressure
  5. customSilica gel column separation
  6. customthus obtaining a compound from which the solvent
  7. customwas then removed under reduced pressure
  8. customdrying

Sources & evidence

ORD record
ord-93dd3badfbed48a3b8590f7df6e018d2
Source dataset
uspto-grants-2016_03
Patent number
US09278986B2

Linked notes

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