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Ethanol → 2,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazole

HRID 1753705
노트
인쇄 미리보기

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HRID 1753705 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]1([N:22]2[C:34]3[CH:33]=[C:32](B4OC(C)(C)C(C)(C)O4)[CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:26][CH:27]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:53]([O-:56])([O-])=O.[Na+].[Na+].[CH3:59][CH2:60]O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:32]2[CH:31]=[CH:30][C:29]3[C:28]4[C:23](=[CH:24][C:25]([C:2]5[CH:7]=[CH:6][C:5]([O:56][CH3:53])=[CH:4][C:3]=5[C:59]5[CH:60]=[CH:12][CH:11]=[CH:10][CH:15]=5)=[CH:26][CH:27]=4)[N:22]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:34]=3[CH:33]=2)=[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:4]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 675132132-Bromo-5-methoxy-1,1'-biphenylHCID 902975249-Phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

생성물 1

HCID 903427912,7-bis(5-methoxybiphenyl-2-yl)-9-phenyl-9H-carbazole수율 67%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

A mixture of 10 g (38.2 mmol) of 2-bromo-5-methoxybiphenyl, 8.6 g (17.4 mmol) of 9-phenyl-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole, 0.4 g (0.35 mmol) of tetrakis(triphenylphosphine)palladium, 30 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 12 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The reaction mixture was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (7.1 g, 11.7 mmol, 67%).

후처리

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate and water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuum
  7. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

출처 및 근거

ORD 기록
ord-da192fb348db453ba07d52f4efd603be
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09166177B2

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