Sodium Carbonate → 4-Fluoro-3'-ethoxy-3-nitrobiphenyl

HRID 24458

Reaktionsgleichung

Reaktionsgleichung von HRID 24458
[CH2:1]([O:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)[CH3:2].Br[C:14]1[CH:15]=[CH:16][C:17]([F:23])=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[F:23][C:17]1[CH:16]=[CH:15][C:14]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)=[CH:19][C:18]=1[N+:20]([O-:22])=[O:21]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 27739203-Ethoxybenzeneboronic acid

Produkt 1

HCID 105633474-Fluoro-3'-ethoxy-3-nitrobiphenylAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0.8 g) was added to a mixture of 4.2 g of 3-ethoxyphenylboronic acid, 5.0 g of 5-bromo-2-fluoronitrobenzene and 22 ml of 2 M sodium carbonate solution in 50 ml of toluene and 50 ml of ethanol. The mixture was heated to reflux for 2 hours. The cooled mixture was concentrated, water was added and the mixture was extracted twice with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried, and concentrated. The residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give 5.3 g (90% yield) of crude 4-fluoro-3′-ethoxy-3-nitrobiphenyl as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. concentrationThe cooled mixture was concentrated
  4. additionwater was added
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe ethyl acetate layer was washed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel (5% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ff598d37ca9c4e469895bf384da9cbd7
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855730B2

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