Ethanol → 8-Bromo-2-phenylquinoline

HRID 1056054

Reaktionsgleichung

Reaktionsgleichung von HRID 1056054
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([Br:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCO.C([O-])([O-])=O.[Na+].[Na+].[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.CCOC(C)=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.O>[Br:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:11]=[CH:10]2

Komponenten

9

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 459259512,8-Dibromoquinoline

Produkt 1

HCID 707004958-Bromo-2-phenylquinolineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2,8-dibromoquinoline (1.0 g, 3.49 mmol), Pd(PPh3)4 (0.2 g, 0.174 mmol) in toluene:EtOH:H2O (10 mL:1 mL:1 mL) under argon atmosphere was added Na2CO3 (0.44 g, 4.18 mmol) and phenyl boronic acid (0.507 g, 4.18 mmol) and the reaction was heated to reflux for 24 h. The mixture was cooled to RT and diluted with EtOAc (50 mL), washed with water and brine (50 mL). The organic layer was dried, filtered and concentrated. The residue was purified by column chromatography (10:1 hexane:EtOAc) to give 8-bromo-2-phenylquinoline (0.75 g, 76%) as pale brown oil. MS (ESI, pos. ion) m/z: 284.0 (M+1).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 24 h
  3. washwashed with water and brine (50 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (10:1 hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-317e579907d64a4197e1aefdb43fc8d2
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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