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

HRID 1021170

反応式

HRID 1021170 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7e5407e0152849ab8e1f57f1f6b24da6
出典データセット
uspto-grants-2014_05
特許番号
US08716484B1

関連ノート

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