Cesium carbonate → 2-bromo-9,10-di(2-naphthyl)-6-(2-phenyl-1H-benzimidazol-1-yl)anthracene

HRID 1172784Notes

Reaction equation

HRID 1172784 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][C:9](Br)=[CH:8][CH:7]=3)[CH:3]=1.[C:37]1([C:43]2[NH:47][C:46]3[CH:48]=[CH:49][CH:50]=[CH:51][C:45]=3[N:44]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1C2C(=CC=C3C=2N=NC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.[Cu](I)I>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][C:9]([N:47]2[C:46]4[CH:48]=[CH:49][CH:50]=[CH:51][C:45]=4[N:44]=[C:43]2[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:8][CH:7]=3)[CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 128552-PhenylbenzimidazoleHCID 601987Benzo[h]cinnolineHCID 224978022,6-Dibromo-9,10-di(naphthalen-2-yl)anthracene

Product 1

HCID 231602402-bromo-9,10-di(2-naphthyl)-6-(2-phenyl-1H-benzimidazol-1-yl)anthraceneYield 36%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

5.9 g (10 mmol) of 2,6-dibromo-9,10-di(2-naphthyl)anthracene, 2.2 g (11 mmol) of 2-phenyl-1H-benzimidazole, 0.19 g (1.0 mmol) of copper iodide, and 3.6 g (2.0 mmol) of 9,10-phenanthroline were dissolved into a 2 M solution of cesium carbonate in dimethylformamide (DMF), and the whole was refluxed under heating for 48 hours in an argon atmosphere. After the completion of the reaction, the resultant was filtered. The filtrate was poured into 1 L of 10-mass % hydrochloric acid, and the whole was extracted with methylene chloride. An organic layer was taken out and dried with magnesium sulfate, and then the solvent was distilled off under reduced pressure. The resultant solid was purified by means of silica gel column chromatography to obtain 2.5 g of a pale yellow solid (36% yield).

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 48 hours in an argon atmosphere
  3. customAfter the completion of the reaction
  4. filtrationthe resultant was filtered
  5. additionThe filtrate was poured into 1 L of 10-mass % hydrochloric acid
  6. extractionthe whole was extracted with methylene chloride
  7. dry with materialdried with magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant solid was purified by means of silica gel column chromatography

Sources & evidence

ORD record
ord-b9a2c934f5904d598f71feef02a64fe4
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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