Carbazole → HCID 57879967, compound

HRID 1816865Notes

Reaction equation

HRID 1816865 reaction equation
N[CH:2]([NH2:4])[CH3:3].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:14]1[CH:19]=[C:18]([Br:20])[C:17](Br)=[CH:16][C:15]=1[Br:22].[CH:23]1[C:35]2[NH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1>[Cu](I)I.O1CCOCC1>[Br:22][C:15]1[C:14]([N:34]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:35]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][C:18]([Br:20])=[C:17]([N:4]2[C:2]3[CH:3]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:35]=3)[CH:16]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 124861,2,4,5-TetrabromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 5242187Ethane-1,1-diamine

Product 1

HCID 57879967HCID 57879967, compoundYield 5.2%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1.16 g (6.1 mmole) of copper iodide and 200 ml of anhydrous dioxane were put in a three-necked flask of 300 ml, 0.41 ml (6.1 mmole) of diaminoethane was dropped at room temperature under nitrogen flow, and the mixture was stirred for 15 minutes at room temperature and heated to 60° C. This solution was allowed to cool to room temperature, 56.8 g (244 mmole) of potassium phosphate, 12.0 g (30.5 mmole) of 1,2,4,5-tetrabromobenzene and 40.8 g (244 mmole) carbazole were added, and heated with stirring at 80° C. under nitrogen flow for 48 hours. After the reaction was completed, the reaction mixture was hot-filtered using Celite to remove insoluble matter. The filtrate was concentrated under reduced pressure. The residue was refined by NH-modified silica gel silica gel column chromatography (eluent:hexane/toluene: 1/2). The obtained crystal was repeatedly recrystallized from toluene and chloroform to give 0.90 g of a white crystal of 1,4-dibromo-3,6-di(carbazole-9-yl)benzene (yield: 5.2%). By reacting two equivalent weight of 4-(2-phenylindole-1-yl)phenyl boronic acid with this 1,4-dibromo-3,6-di(carbazole-9-yl)benzene, 1,4-di(carbazole-9-yl)-2,5-bis{4-(2-phenylindole-1-yl)phenyl}benzene was obtained. The melting point of this compound was 376° C., and the glass transition temperature was 184° C.

Workup

  1. additionwas dropped at room temperature under nitrogen flow
  2. temperatureheated to 60° C
  3. temperatureto cool to room temperature
  4. temperatureheated
  5. stirringwith stirring at 80° C. under nitrogen flow for 48 hours
  6. filtrationthe reaction mixture was hot-filtered
  7. customto remove insoluble matter
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe obtained crystal was repeatedly recrystallized from toluene and chloroform

Sources & evidence

ORD record
ord-6579419ae27f4418bd34a4bf282f7b07
Source dataset
uspto-grants-2009_10
Patent number
US07597955B2

Reaction notes

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