4-Fluorophenylboronic acid → HCID 23499548, Verbindung

HRID 1251881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251881
C(=O)([O-])O.[Na+].[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10](OS(C(F)(F)F)(=O)=O)[CH:9]=1.[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([C:30]2[CH:31]=[CH:32][C:27]([F:26])=[CH:28][CH:29]=2)[CH:9]=1

Komponenten

6

Edukt 3

HCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 10710352Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate

Produkt 1

HCID 23499548HCID 23499548, VerbindungAusbeute 138,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Saturated aqueous sodium hydrogen carbonate solution (50 ml) was added to a solution of methyl 4-methoxy-2-trifluoromethylsulfonyloxybenzoate (6.3 g; 0.02 mol) and 4-fluorobenzeneboronic acid (3.36 g; 0.024 mol) in DME (150 ml) at ambient temperature under an argon atmosphere. Tetrakis(triphenylphosphine) palladium (928 mg; 0.8 mmol) was then added and the reaction heated at reflux for 3.5 hours to give a homogeneous solution. After cooling to ambient temperature, the reaction was partitioned between ethyl acetate and water. The organic phase was washed with 2N HCl, water and brine, filtered through 1PS filter paper and the solvent removed in vacuo to give methyl 4-methoxy-2-(4-fluorophenyl)benzoate as a yellow oily solid (7.2 g) which was used without further purification.

Aufarbeitung

  1. temperaturethe reaction heated
  2. temperatureat reflux for 3.5 hours
  3. customto give a homogeneous solution
  4. customthe reaction was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with 2N HCl, water and brine
  6. filtrationfiltered through 1PS filter paper
  7. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c938219961fe4e98a5943115c9105669
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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