Potassium Carbonate → 3',4',5'-Trifluoro-[1,1'-biphenyl]-4-carbaldehyde

HRID 1406828

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].[CH:17]([C:19]1[CH:24]=[CH:23][C:22](OB(O)O)=[CH:21][CH:20]=1)=[O:18]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:22]2[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

In a nitrogen atmosphere, a solution prepared by mixing 15.00 g of 3,4,5-trifluorobromobenzene, 0.25 g of tetrakis-triphenylphosphine palladium, 30 mL of an aqueous potassium carbonate solution (2 mol/L), and 75 mL of THF was heated to 60° C., and 10.71 g of 4-formylphenylboric acid was added to the solution over 20 minutes. After the resultant mixture was stirred at 60° C. for 3 hours, the mixture was allowed to cool, and an organic layer was separated by adding hexane. The organic layer was washed with saturated brine and dried by adding sodium sulfate, and then the solvent was distilled off under reduced pressure. As a result of purification by silica gel column chromatography, 14.77 g of 4-(3,4,5-trifluorophenyl)benzaldehyde was yielded.

Aufarbeitung

customIn a nitrogen atmosphere, a solution prepared
temperatureto cool
customan organic layer was separated
additionby adding hexane
washThe organic layer was washed with saturated brine
customdried
additionby adding sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customAs a result of purification by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-1f4bff464cbe48f4820367ccdde28900
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08916718B2

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