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

HRID 2206829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2206829
[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-1ea1a8aaba2847c2ac33d8fdf600c354
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09373792B2

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