Ethanol → 2-bromo-7-(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluorene

HRID 1753702Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1753702
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[CH:22][C:23](B(O)O)=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:25]=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>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:7]3[C:6](=[CH:11][C:10]([C:23]4[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:25][C:24]=4[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[CH:9][CH:8]=3)[C:5]([CH3:16])([CH3:17])[C:4]=2[CH:3]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 121238762,7-Dibromo-9,9-dimethylfluoreneHCID 85664000(4-Methoxy-2-phenylphenyl)boronic acid

Produkt 1

HCID 867300022-bromo-7-(5-methoxybiphenyl-2-yl)-9,9-dimethyl-9H-fluoreneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A mixture of 3.52 g (10 mmol) of 2,7-dibromo-9,9-dimethyl-9H-fluorene, 2.75 g (12 mmol) of 5-methoxybiphenyl-2-ylboronic acid, 0.12 g (0.1 mmol) of tetrakis(triphenylphosphine)palladium, 15 ml of 2M Na2CO3, 20 ml of EtOH and 60 ml toluene was degassed and placed under nitrogen, and then heated at 110° C. for 8 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 (3.4 g, 7.5 mmol, 75%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-1ef20d9de3084f75a594e1b80ff4b744
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09166177B2

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