Sodium Carbonate → 5-(Furan-2-yl)-2,3-dimethoxybenzonitrile

HRID 56515Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56515
Br[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8].[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1B(O)O.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 2734357Furan-2-boronic acidHCID 226838165-Bromo-2,3-dimethoxybenzonitrile

Produkt 1

HCID 584320135-(Furan-2-yl)-2,3-dimethoxybenzonitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a mixture of 5-bromo-2,3-dimethoxybenzonitrile (0.958 g, 4.0 mmol), 2-furylboronic acid (0.53 g, 4.7 mmol), dioxane (24 mL), H2O (8 mL) and Na2CO3 (1.1 g, 10.4 mmol) was added tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol). The mixture was degassed by alternately putting under house vacuum and argon three times for several minutes each then heated at 85° C. under argon for 16.5 hrs. After cooling to room temperature, the mixture was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O and brine, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (0-20% EtOAc-hexanes) provided 5-(furan-2-yl)-2,3-dimethoxybenzonitrile as a white solid (0.85 g, 94% yield).

Aufarbeitung

  1. customThe mixture was degassed
  2. waitby alternately putting under house vacuum and argon three times for several minutes
  3. temperatureAfter cooling to room temperature
  4. additionthe mixture was diluted with H2O
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with H2O and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by chromatography (0-20% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-49250adb226a444ab760551ad394d451
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434707B2

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