Sodium Carbonate → 2-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthalene

HRID 539259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539259
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1B(O)O)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=1I.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:23]1[CH:22]=[C:21]([Br:24])[CH:20]=[CH:19][C:18]=1[F:17])[CH3:2]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27827504-Bromo-1-fluoro-2-iodobenzeneHCID 16213801(2-Ethoxynaphthalen-1-yl)boronic acid

Produkt 1

HCID 677732662-Ethoxy-1-(2-fluoro-5-bromophenyl)naphthaleneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

In the atmosphere of argon, 22.7 g of 2-ethoxynaphthalene-1-boronic acid, 30.0 g of 2-fluoro-5-bromoiodobenzene, 2.31 g of tetrakistriphenylphosphine palladium (0), 300 mL of toluene and 150 mL of an aqueous 2M 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 concentrated. Residues were purified by means of silica gel column chromatography, whereby 24.1 g (yield: 70%) of 2-ethoxy-1-(2-fluoro-5-bromophenyl)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 means of silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-607977f1f1c34210a31e5247cf806a48
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08866135B2

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