Carbazole → 9-(3-Bromophenyl)-9H-carbazole

HRID 2039419Notes

Reaction equation

HRID 2039419 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.I[C:15]1[CH:16]=[C:17]([Br:21])[CH:18]=[CH:19][CH:20]=1.[Na]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1(C)C=CC=C(C)C=1>[Br:21][C:17]1[CH:16]=[C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 11561Benzene, 1-bromo-3-iodo-HCID 5360545Sodium

Product 1

HCID 586908889-(3-Bromophenyl)-9H-carbazoleYield 51.1%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7929M-XyleneSolvent

Procedure

The 300 mL round bottom flask, equipped with magnetic stirrer and refluxed condenser, was charged with carbazole (7.1 g, 42.5 mmol), 3-iodobromobenzene (25.00 g, 88 mmol), Pd2(dba)3 (800 mg, 1 mol %), dppf (1′,1′-bis(diphenylphosphino)ferrocene (975 mg, 2 mol %), sodium t-buthoxide (6.3 g) and m-xylene (100 ml). The reaction mixture was heated to reflux and stirred under nitrogen atmosphere for 48 hours. Then reaction was cooled down to room temperature, filtered through silica plug and evaporated. The residue was subjected to column chromatography on silica gel, eluent gradient mixture hexane-hexane/ethyl acetate mixture 9:1, providing 7.00 g of 9-(3-bromo-phenyl)-9H-carbazole as white solid, structure was confirmed by NMR and GCMS spectroscopy.

Workup

  1. customThe 300 mL round bottom flask, equipped with magnetic stirrer
  2. temperaturerefluxed condenser
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. customThen reaction
  6. filtrationfiltered through silica plug
  7. customevaporated

Sources & evidence

ORD record
ord-1b95c4cdbce0439ead0edd905a64a53e
Source dataset
uspto-grants-2013_11
Patent number
US08580402B2

Reaction notes

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