1,4-Dibromobenzene → HCID 86762388, 화합물

HRID 1021175노트

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HRID 1021175 반응식
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([N:7]([C:30]2[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=2)[C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 78041,4-DibromobenzeneHCID 23676156Sodium t-butoxideHCID 86762387Biphenyl-4-yl-biphenyl-2-yl-amin

생성물 1

HCID 86762388HCID 86762388, 화합물수율 87%

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매

실험 절차

Toluene (500 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.4 g, 1.7 mmol) and Pd(OAc)2 (0.10 g, 0.42 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (6.7 g, 21.0 mmol), 1,4-dibromobenzene (14.9 g, 63.0 mmol), sodium tert-butoxide (4.0 g, 42.0 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 (containing 0.5% triethylamine). The solvent was removed in vacuo and the residue was purified by flash chromatography using 10-20% toluene/hexane (containing 0.5% triethylamine) to afford N-([1,1′-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1′-biphenyl]-2-amine (8.7 g, 87% yield) as a white solid.

후처리

  1. customToluene (500 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 (containing 0.5% triethylamine)
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-fd0095f01a244f86af9fc3ad4e05623c
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716484B1

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