Sodium Carbonate → 5-Bromo-2-fluoro-2',3'-dimethoxy-2''-fluoro-p-terphenyl

HRID 539256Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539256
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11](B(O)O)=[C:10]([O:17][CH3:18])[C:9]=1[O:19][CH3:20].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][C:23]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([F:21])=[C:27]([C:11]2[CH:12]=[CH:13][C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])=[C:9]([O:19][CH3:20])[C:10]=2[O:17][CH3:18])[CH:26]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 677757472'-Fluoro-2,3-dimethoxybiphenyl-4-boronic acid

Produkt 1

HCID 677757275-Bromo-2-fluoro-2',3'-dimethoxy-2''-fluoro-p-terphenylAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In the atmosphere of argon, 15.2 g of 2′-fluoro-2,3-dimethoxybiphenyl-4-boronic acid, 16.5 g of 2-fluoro-5-bromoiodobenzene, 1.27 g of tetrakistriphenylphosphine palladium (0), 180 mL of toluene and 90 mL of an aqueous 2M sodium carbonate solution were placed in a flask. The resulting solution was stirred with heating under reflux for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate, and concentrated. Residues were purified by means of silica gel column chromatography, whereby 17.8 g (yield: 80%) of 5-bromo-2-fluoro-2′,3′-dimethoxy-2″-fluoro-p-terphenyl was obtained.

Aufarbeitung

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAn aqueous phase was removed
  5. washan organic phase was washed with saturated saline
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. concentrationconcentrated
  8. customResidues were purified by means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e6c1dcb6bb3f455d9017790490222468
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08866135B2

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