4,4'-Dibromobiphenyl → HCID 86762389、化合物

HRID 1021176ノート

反応式

HRID 1021176 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=[CH:24][C:23]([NH:26][C:27]2[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH:21]=1.[Br:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55](Br)=[CH:54][CH:53]=2)=[CH:48][CH:47]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:25]=[CH:24][C:23]([N:26]([C:55]2[CH:54]=[CH:53][C:52]([C:49]3[CH:48]=[CH:47][C:46]([Br:45])=[CH:51][CH:50]=3)=[CH:57][CH:56]=2)[C:27]2[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 71104,4'-DibromobiphenylHCID 11776TriphenylphosphineHCID 23676156Sodium t-butoxideHCID 86762387Biphenyl-4-yl-biphenyl-2-yl-amin

生成物 1

HCID 86762389HCID 86762389、化合物収率 73%

試薬・触媒・溶媒 1

HCID 167845palladium(II) acetate触媒

実験手順

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.2 g, 0.8 mmol) and Pd(OAc)2 (0.05 g, 0.2 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (3.4 g, 10.5 mmol), 4,4′-dibromobiphenyl (6.6 g, 21.0 mmol), sodium tert-butoxide (2.0 g, 21.0 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 20% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (4.2 g, 73% yield) as a white solid.

後処理

  1. customToluene (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-833970d2a5234159b2d01676fe74dfa8
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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