4'-Bromo-2-nitrobiphenyl → 2-Bromo-9H-carbazole

HRID 628214Notes

Reaction equation

HRID 628214 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)=[CH:4][CH:3]=1>P(OCC)(OCC)OCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:14][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 218576474'-Bromo-2-nitrobiphenyl

Product 1

HCID 127170892-Bromo-9H-carbazoleYield 40%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

Around bottom flask was charged with 4′-bromo-2-nitrobiphenyl (100 mmol) and triethyl phosphite (100 mL) and set to reflux under a nitrogen atmosphere for 24 hours. Upon cooling, the solvent was distilled off under vacuum, and the crude product was recrystallized from hot toluene to give 2-bromo-9H-carbazole in 40% yield.

Workup

  1. temperatureto reflux under a nitrogen atmosphere for 24 hours
  2. temperatureUpon cooling
  3. distillationthe solvent was distilled off under vacuum
  4. customthe crude product was recrystallized from hot toluene

Sources & evidence

ORD record
ord-2759e48d8fcd4aee9dc790e05c33ed1e
Source dataset
uspto-grants-2016_04
Patent number
US09312502B2

Reaction notes

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