N,N'-Dimethylethylenediamine → 2-(N,N-diphenylamino)-7-bromo-9,9-dimethylfluorene

HRID 31957Notes

Reaction equation

HRID 31957 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](I)=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[C:18]1([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CNCCNC.CC(C)([O-])C.[Na+]>[Cu](I)I.C1(C)C(C)=CC=CC=1>[C:25]1([N:24]([C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[C:4](=[CH:3][C:2]([Br:1])=[CH:14][CH:13]=4)[C:5]([CH3:17])([CH3:16])[C:6]=3[CH:7]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11487DiphenylamineHCID 23676156Sodium t-butoxideHCID 453821792-Bromo-7-iodo-9,9-dimethyl-9H-fluorene

Product 1

HCID 587297452-(N,N-diphenylamino)-7-bromo-9,9-dimethylfluoreneYield 69.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 7237O-XyleneSolvent

Procedure

Charged under Ar atmosphere were 2-bromo-7-iodo-9,9-dimethylfluorene 20.0 g, diphenylamine 8.46 g, copper iodide 0.476 g, N,N′-dimethylethylene-diamine 0.441 g, sodium t-butoxide 7.21 g and xylene 50 ml, and the mixture was refluxed for 24 hours under heating. After cooled down to room temperature, the mixture was extracted with toluene, and the insoluble matter was filtered. The filtrate was concentrated, and then the concentrate was refined by silica gel chromatography to obtain 15.4 g of a yellow solid matter of 2-(N,N-diphenylamino)-7-bromo-9,9-dimethylfluorene.

Workup

  1. additionCharged under Ar atmosphere
  2. temperaturethe mixture was refluxed for 24 hours
  3. temperatureunder heating
  4. extractionthe mixture was extracted with toluene
  5. filtrationthe insoluble matter was filtered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9fd63b03482f4e93a36ae9d35def82bf
Source dataset
uspto-grants-2008_09
Patent number
US07425654B2

Reaction notes

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