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

HRID 2209334Notes

Reaction equation

HRID 2209334 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](Br)[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>[Cu].CN(C)C=O>[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

6

Reactant 3

HCID 6854CarbazoleHCID 79271,3-DibromobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 586908889-(3-Bromophenyl)-9H-carbazoleYield 71%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

(see Kido, J.; Su, S. -J.; Sasabe, H.; Takeda, T.; Chem. Mater. 2008, 20(5), 1691-1693, which is incorporated by reference herein for its relevant teachings) was prepared as follows: a mixture of carbazole (4.000 g, 23.92 mmol), 1,3-dibromobenzene (14.11 g, 59.81 mmol), K2CO3 (9.919 g, 71.77 mmol), copper powder (4.561 g, 71.77 mmol) and anhydrous N,N-dimethylformamide (DMF) (120 mL) was degassed with argon for 1 h. while stirring. The reaction mixture was then maintained under argon at 130° C. while stirring for 4 days until TLC (SiO2, 4:1 hexanes-dichloromethane) indicated consumption of the starting material. Upon cooling to RT, about 300 mL dichloromethane was added, the crude mixture filtered, the filtrant wash with an additional 200 mL dichloromethane, and the filtrate concentrated in vacuo. The resulting residue was then purified by flash chromatography (SiO2, hexanes) to yield Compound 3 (5.47 g, 71%) as a colorless oil.

Workup

  1. custom(see Kido, J.; Su, S. -J.; Sasabe, H.; Takeda, T.; Chem. Mater. 2008, 20(5), 1691-1693, which is incorporated by reference herein for its relevant teachings) was prepared
  2. customwas degassed with argon for 1 h.
  3. stirringwhile stirring for 4 days until TLC (SiO2, 4:1 hexanes-dichloromethane)
  4. customconsumption of the starting material
  5. temperatureUpon cooling to RT
  6. additionabout 300 mL dichloromethane was added
  7. filtrationthe crude mixture filtered
  8. washthe filtrant wash with an additional 200 mL dichloromethane
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe resulting residue was then purified by flash chromatography (SiO2, hexanes)

Sources & evidence

ORD record
ord-f45797576c154b7083d26e98e8962609
Source dataset
uspto-grants-2016_06
Patent number
US09379336B2

Reaction notes

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