Ethanol → 9-Bromo-10-(naphthalen-2-yl)anthracene

HRID 1775391

반응식

HRID 1775391 반응식
Br[C:2]1[C:3]2[C:8]([C:9]([Br:16])=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1B(O)O.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>[Br:16][C:9]1[C:10]2[C:15]([C:2]([C:19]3[CH:18]=[CH:17][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]=3)=[C:3]3[C:8]=1[CH:7]=[CH:6][CH:5]=[CH:4]3)=[CH:14][CH:13]=[CH:12][CH:11]=2

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 682269,10-DibromoanthraceneHCID 2734375(Naphthalen-2-yl)boronic acid

생성물 1

HCID 161162639-Bromo-10-(naphthalen-2-yl)anthracene수율 61%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A mixture of 15 g (44.6 mmol) of 9,10-dibromoanthracene, 7.7 g (44.6 mmol) of naphthalen-2-ylboronic acid, 0.52 g (0.446 mmol) of Tetrakis(triphenylphosphine)Palladium, 33 ml of 2M Na2CO3, 60 ml of EtOH and 150 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 h. After the reaction finish, 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 10.4 g (61%) as a yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-4c74d78cba8e4e248586496270730689
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260363B2

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