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

HRID 2177656Notes

Reaction equation

HRID 2177656 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]=[C:17](I)[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>C(Cl)Cl.[Cu].C1CCCCC1.C(Cl)Cl>[Br:14][C:15]1[CH:16]=[C:17]([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:18]=[CH:19][CH:20]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-

Product 1

HCID 586908889-(3-Bromophenyl)-9H-carbazoleYield 82.4%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6344DichloromethaneSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Conditions

Temperature
150 °C

Procedure

Under nitrogen, carbazole (24.3 g, 1 eq.) is added to a flask together with 1-bromo-3-iodobenzene (98%; 75.3 g, 1.9 eq.), potassium carbonate (48.2 g, 2.5 eq.) and copper (1.77 g, 0.1 eq.). The reaction is heated to 150° C. and stirred at 150° C. for 48 h. The mixture is cooled to room temperature and diluted with 150 mL of methylene chloride. 100 mL of demineralized water are added to the mixture, which is stirred. Removal of the aqueous phase is followed by washing a further 2× with demineralized water (100 mL). The organic phase is dried over sodium sulfate and concentrated. The excess 1-bromo-3-iodobenzene is distilled off under reduced pressure. LC (SiO2; cyclohexane/methylene chloride 95:5) gives 37.1 g of product (82.4% yield).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. stirringis stirred
  3. customRemoval of the aqueous phase
  4. washby washing a further 2× with demineralized water (100 mL)
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. distillationThe excess 1-bromo-3-iodobenzene is distilled off under reduced pressure

Sources & evidence

ORD record
ord-2b5d18e84d704e6ab53ff9e2691e344b
Source dataset
uspto-grants-2015_06
Patent number
US09067919B2

Reaction notes

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