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Sodium Carbonate → 2-Methoxy-3-(2-fluorophenyl)naphthalene

HRID 539260
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 539260
[CH3:1][O:2][C:3]1[C:4](B(O)O)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1Br.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:1][O:2][C:3]1[C:4]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[F:16])=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=1
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Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 612591-Bromo-2-fluorobenzeneHCID 108889523-Methoxynaphthalene-2-boronic acid

Produkt 1

HCID 677759332-Methoxy-3-(2-fluorophenyl)naphthaleneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In the atmosphere of argon, 14.3 g of 3-methoxynaphthalene-2-boronic acid, 12.4 g of 2-fluorobromobenzene, 1.64 g of tetrakistriphenylphosphine palladium (0), 220 mL of 1,2-dimethoxyethane, 110 mL of a 2M aqueous solution of sodium carbonate were placed in a flask, and the resulting mixture 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 then an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and then concentrated. Residues were purified by silica gel column chromatography, whereby 13.4 g (yield: 75%) of 2-methoxy-3-(2-fluorophenyl)naphthalene 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 silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-94a5170115c64375802ea07211f86e1c
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08866135B2

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