4-Fluorophenylboronic acid → HCID 18444638, Verbindung

HRID 1786612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786612
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.I[C:12]1[CH:25]=[CH:24][C:15]([O:16][CH2:17][C:18]2[CH:22]=[CH:21][O:20][C:19]=2[CH3:23])=[CH:14][CH:13]=1.C([O-])(=O)C.[K+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:22]=[CH:21][O:20][C:19]=3[CH3:23])=[CH:24][CH:25]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 2856454-Fluorophenylboronic acidHCID 517044Potassium AcetateHCID 18444641HCID 18444641, Verbindung

Produkt 1

HCID 18444638HCID 18444638, VerbindungAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of (4-fluoro-phenyl)-boronic acid (300 mg, 2.1 mmoles), 3-(4-iodophenoxymethyl)-2-methyl-furan (123) (500 mg, 1.6 mmoles) and potassium acetate (0.6 g) in N,N-dimethylformamide (70 mL) was degassed, treated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg) and the mixture was agitated at 95° C. for 12 hours under an argon atmosphere. The mixture was concentrated in vacuo, partitioned between water (100 ml) and diethyl ether (200 ml). The aqueous phase was re-extracted with diethyl ether, and the combined etheral phases were dried and evaporated. The residue was purified by flash chromatography, using diethyl ether as eluent, to afford compound 124 (200 mg) as a solid. This material was used directly.

Aufarbeitung

  1. customwas degassed
  2. additiontreated with [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (90 mg)
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between water (100 ml) and diethyl ether (200 ml)
  5. extractionThe aqueous phase was re-extracted with diethyl ether
  6. customthe combined etheral phases were dried
  7. customevaporated
  8. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-30912a3d6da24e659691cf8a35221043
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507754B2

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