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

HRID 31957
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HRID 31957 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 83717
Copper iodide
촉매
HCID 7237O-Xylene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9fd63b03482f4e93a36ae9d35def82bf
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425654B2

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