Potassium Phosphate, Tribasic → HCID 87088131, Verbindung

HRID 402763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402763
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:50][C:51]1[C:56]([F:57])=[C:55]([F:58])[CH:54]=[CH:53][C:52]=1B(O)O>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:7]1[CH:6]=[C:3]([CH:4]=[O:5])[C:2]([C:54]2[CH:53]=[CH:52][C:51]([F:50])=[C:56]([F:57])[C:55]=2[F:58])=[CH:9][CH:8]=1)[CH3:12]

Komponenten

7

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 27832802,3,4-Trifluorobenzeneboronic acidHCID 30164192-Bromo-5-ethoxybenzaldehydeHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Produkt 1

HCID 87088131HCID 87088131, VerbindungAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a degassed solution of 2-bromo-5-ethoxybenzaldehye (300 mg, 1.31 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (53.8 mg, 0.131 mmol; S-Phos ligand), palladium (II) acetate (14.7 mg, 0.065 mmol) in THF (8 mL) were added K3PO4 (834 mg, 3.93 mmol) and (2,3,4-trifluorophenyl)boronic acid (276, 1.57 mmol). Reaction mixture was stirred at 70° C. under a N2 atmosphere for 16 hours, cooled to room temperature and then filtered. The filtrate was concentrated by evaporation under reduced pressure. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to provide the title intermediate (255 mg) as white solid.

Aufarbeitung

  1. customReaction mixture
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. customThe residue was purified on a silica gel column
  6. washeluting with 5 to 10% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b6fd571bca3d487695db922439a541ef
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742110B2

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