4,4'-Dibromobiphenyl → HCID 86762389, 화합물

HRID 1021176노트

반응식

HRID 1021176 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 86762389HCID 86762389, 화합물수율 73%

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-833970d2a5234159b2d01676fe74dfa8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716484B1

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