2-Aminobiphenyl → Biphenyl-4-yl-biphenyl-2-yl-amin

HRID 1021174ノート

反応式

HRID 1021174 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:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]([NH2:36])=[CH:32][CH:33]=[CH:34][CH:35]=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:36][C:31]2[C:30]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:18][CH:19]=1

参加物

6

反応物 4

HCID 70152-AminobiphenylHCID 153224-IodobiphenylHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

生成物 1

HCID 86762387Biphenyl-4-yl-biphenyl-2-yl-amin収率 790.8%

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 (3.0 g, 7.2 mmol) and Pd2(dba)3 (1.6 g, 1.8 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′-biphenyl]-2-amine (10.1 g, 60.0 mmol), 4-iodobiphenyl (16.8 g, 60.0 mmol), sodium tert-butoxide (11.5 g, 120.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 12 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 30% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (18.3 g, 95% 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 12 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-36c60ae0480a4ee59b8a80f284453c40
出典データセット
uspto-grants-2014_05
特許番号
US08716484B1

反応ノート

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