Aniline → 9,9-Dibutyl-n-(9,9-dibutylfluorenyl)-n-phenylfluorenamine

HRID 1029065Notes

Reaction equation

HRID 1029065 reaction equation
[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH3:22])[C:17]2[CH:16]=[C:15](I)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].C1O[CH2:52][CH2:51]OCCOCCOCCOCCOC1>CN(C)C=O.[Cu]>[CH2:1]([C:5]1([CH2:19][CH2:20][CH2:21][CH3:22])[C:17]2[C:16]([N:23]([C:7]3[C:6]4[C:5]([CH2:19][CH2:20][CH2:51][CH3:52])([CH2:1][CH2:2][CH2:3][CH3:4])[C:17]5[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=5)[C:11]=4[CH:10]=[CH:9][CH:8]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 6115AnilineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 230728539,9-dibutyl-2-iodo-9H-fluorene

Product 1

HCID 689823659,9-Dibutyl-n-(9,9-dibutylfluorenyl)-n-phenylfluorenamine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

40 parts of 9,9-dibutyl-2-iodofluorene, 3.7 parts of aniline, 30 parts of potassium carbonate, 6 parts of copper powders (200 meshes), and 0.87 parts of 18-crown-6 were dissolved in 50 parts of dimethylformamide (DMF), and the obtained solution was reacted in a nitrogen atmosphere at 160° C. for 24 hours. After completion of the reaction, the reaction product was filtrated, and the filtrate was then extracted with ethyl acetate-water. The ethyl acetate phase was dried over magnesium sulfate, and the ethyl acetate was then distilled away, thereby obtaining a brown tarry substance. This brown tarry substance was separated and purified by column chromatography (hexane-ethyl acetate) to obtain 15 parts of 9,9-dibutyl-N-(9,9-dibutylfluorenyl)-N-phenylfluorenamine (the following Compound (344)) in the form of a colorless crystal.

Workup

  1. customthe obtained solution was reacted in a nitrogen atmosphere at 160° C. for 24 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction product was filtrated
  4. extractionthe filtrate was then extracted with ethyl acetate-water
  5. dry with materialThe ethyl acetate phase was dried over magnesium sulfate
  6. distillationthe ethyl acetate was then distilled away
  7. customobtaining a brown tarry substance
  8. customThis brown tarry substance was separated
  9. custompurified by column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-19dfb8e0021349e6af89e33c4f1002f8
Source dataset
uspto-grants-2014_05
Patent number
US08735720B2

Reaction notes

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