4-Iodobiphenyl → N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-4'-amine

HRID 1021170

반응식

HRID 1021170 반응식
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19](OC)=[CH:18][CH:17]=[CH:16][C:15]=2OC)CCCCC1.[C:30]1([C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[C:38]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.IC1C=CC(C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:14]1([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:17]([NH:42][C:39]2[CH:40]=[CH:41][C:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:37][C:38]=2[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 153224-IodobiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 123166382,4-DiphenylanilineHCID 23676156Sodium t-butoxide

생성물 1

HCID 86762383N-([1,1'-biphenyl]-4-yl)-[1,1':3',1''-terphenyl]-4'-amine수율 840.5%

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

실험 절차

Xylene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.8 g, 4.4 mmol) and Pd2(dba)3 (1.0 g, 1.1 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′:3′,1″-terphenyl]-4′-amine (9.8 g, 40.0 mmol), 4-iodobiphenyl (10.3 g, 36.7 mmol), sodium tert-butoxide (7.0 g, 73.4 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 13 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using 40-60% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-4′-amine (14.7 g, 92% yield) as a white solid.

후처리

  1. customXylene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 13 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with toluene
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-7e5407e0152849ab8e1f57f1f6b24da6
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716484B1

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