1,10-Phenanthroline → 4-[9-(4'-Carbazol-9-ylbiphenyl-4-yl)-9H-carbazol-2-yl]benzaldehyde

HRID 1628372Notes

Reaction equation

HRID 1628372 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][C:2]=1C1(C=CC=CC1)C=O.Br[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([N:35]3[C:47]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[C:41]4[C:36]3=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1.N1[C:61]2[C:52](=[CH:53][CH:54]=[C:55]3[C:60]=2N=CC=C3)[CH:51]=CC=1.C(=O)([O-])[O-:63].[K+].[K+]>ClC1C=CC=CC=1Cl>[CH:46]1[C:47]2[N:35]([C:32]3[CH:33]=[CH:34][C:29]([C:26]4[CH:27]=[CH:28][C:23]([N:12]5[C:4]6[CH:3]=[C:2]([C:55]7[CH:60]=[CH:61][C:52]([CH:51]=[O:63])=[CH:53][CH:54]=7)[CH:1]=[CH:13][C:5]=6[C:6]6[C:11]5=[CH:10][CH:9]=[CH:8][CH:7]=6)=[CH:24][CH:25]=4)=[CH:30][CH:31]=3)[C:36]3[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]=2[CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 13181,10-PhenanthrolineHCID 11430Potassium CarbonateHCID 588923869-(4'-Bromo-4-biphenylyl)carbazoleHCID 866917681-(9H-carbazol-2-yl)benzaldehyde

Product 1

HCID 866917674-[9-(4'-Carbazol-9-ylbiphenyl-4-yl)-9H-carbazol-2-yl]benzaldehydeYield 138.7%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

2.27 g (0.008367 mol) of 1-(9H-carbazol-2-yl)benzaldehyde, 4.0 g (0.010 mol) of 9-(4′-bromobiphenyl-4-yl)-9H-carbazole, 3.79 g of Cu bronze, 0.53 g (0.00294 mol) of 1,10-phenanthroline and 11.39 g (0.082 mol) of potassium carbonate are initially introduced. The solids are dissolved in 53 ml of 1,2-dichlorobenzene and stirred under reflux for 2 days. After filtration through Celite, the mixture is evaporated to dryness. Column chromatography with toluene/hexane as eluent give 2.4 g (49%) of clean product.

Workup

  1. temperatureunder reflux for 2 days
  2. filtrationAfter filtration through Celite
  3. customthe mixture is evaporated to dryness

Sources & evidence

ORD record
ord-fb627899346844849170086b4dffd440
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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