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Ethanol → 1-(5-Methoxybiphenyl-2-yl)pyrene

HRID 1852554
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HRID 1852554 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(B(O)O)[C:29]2[C:30]3=[C:31]4[C:26](=[CH:27][CH:28]=2)[CH:25]=[CH:24][CH:23]=[C:22]4[CH:21]=[CH:20][C:19]3=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].CCO>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:23]2[C:22]3[C:31]4=[C:30]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:29]5[CH:28]=[CH:27][C:26]4=[CH:25][CH:24]=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 5084102Pyren-1-ylboronic acidHCID 675132132-Bromo-5-methoxy-1,1'-biphenyl

생성물 1

HCID 867236161-(5-Methoxybiphenyl-2-yl)pyrene수율 76.1%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 1140Toluene용매

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온도
90 °C

실험 절차

A mixture of 11.1 g (42.4 mmol) of 2-bromo-5-methoxybiphenyl, 10.43 g (42.4 mmol) of pyren-1-ylboronic acid, 0.5 g (0.424 mmol) of tetrakis(triphenylphosphine)palladium, 32 ml of 2M Na2CO3, 80 ml of EtOH and 160 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After finishing the reaction, the mixture was allowed to cool to room temperature. The organic layer was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 12.4 g (76%) as a white solid.

후처리

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

출처 및 근거

ORD 기록
ord-b05b47b058f74bc1a91a73e0fd66bb4d
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962160B2

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