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

HRID 1057451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057451
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([F:22])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=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:22][C:16]1[CH:15]=[CH:14][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][C:17]=1[N+:19]([O-:21])=[O:20]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Produkt 1

HCID 107529914-Fluoro-4'-methoxy-3-nitrobiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (1 g) was added to a mixture of 5 g of 4-methoxyphenylboronic acid, 6,6 g of 5-bromo-2-fluoronitrobenzene and 30 mL of 2 M sodium carbonate solution in 50 mL of toluene and 50 mL of ethanol. The mixture was heated to refulux for 2 hours, concentrated, and the residue extracted twice with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried, and concentrated to give a brown oily solid. The solid was chromatographed on silica gel in 5% ethyl acetate in hexane to give crude 4-fluoro-4′-methoxy-3-nitrobiphenyl as a pale yellow solid.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. concentrationconcentrated
  3. extractionthe residue extracted twice with ethyl acetate
  4. washThe ethyl acetate layer was washed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give a brown oily solid
  8. customThe solid was chromatographed on silica gel in 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-b4469b08a33545a7acee5da9cc2091b0
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514981B1

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