Tetrahydrofuran → 3,5-Difluoro-4'-propyl-1,1'-biphenyl

HRID 1406822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1406822
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].C1COCC1.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1>CCCCCC>[F:22][C:23]1[CH:24]=[C:25]([C:7]2[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 1363741-Bromo-4-propylbenzeneHCID 2734338(3,5-Difluorophenyl)boronic acid

Produkt 1

HCID 156387533,5-Difluoro-4'-propyl-1,1'-biphenylAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a nitrogen atmosphere, a solution prepared by mixing 90.33 g of 4-propylbromobenzene, 2.62 g of tetrakis-triphenylphosphine palladium, 240 mL of an aqueous potassium carbonate solution (2 mol/L), and 450 mL of THF was heated to 60° C., and 71.65 g of 3,5-difluorophenylboronic acid was added to the solution over 30 minutes. The resultant mixture was stirred at 60° C. for 30 minutes and then allowed to cool. Then, hexane was added to the mixture to separate an organic layer, and the organic layer was washed with saturated brine and dried by adding sodium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to yield 104.92 g of 3,5-difluoro-1-(4-propylphenyl)benzene.

Aufarbeitung

  1. customIn a nitrogen atmosphere, a solution prepared
  2. temperatureto cool
  3. customto separate an organic layer
  4. washthe organic layer was washed with saturated brine
  5. customdried
  6. additionby adding sodium sulfate
  7. distillationThen, the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-836541e00bdb46cc860a99569269ab0e
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08916718B2

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