Butyl Acrylate → HCID 66733998, Verbindung

HRID 1929615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929615
Br[C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1.[C:11]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])[CH:12]=[CH2:13].C1N2CCN(CC2)C1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[CH2:16]([O:15][C:11](=[O:14])[CH:12]=[CH:13][C:2]1[CH:3]=[C:4]([F:10])[C:5]([CH3:9])=[C:6]([F:8])[CH:7]=1)[CH2:17][CH2:18][CH3:19]

Komponenten

8

Edukt 4

HCID 8846Butyl AcrylateHCID 9237DabcoHCID 11430Potassium CarbonateHCID 27832155-bromo-1,3-difluoro-2-methylbenzene

Produkt 1

HCID 66733998HCID 66733998, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 5-bromo-1,3-difluoro-2-methyl-benzene (6.910 g; 33.379 mmol) in anhydrous DMF (200 ml) were added successively butyl acrylate (7.15 ml; 50.062 mmol), DABCO (157 mg; 1.333 mmol), potassium carbonate (4.612 g; 33.379 mmol), and palladium acetate (150 mg; 0.669 mmol). The resulting brown suspension was heated to 120° C. for 1 h. The reaction mixture was allowed to cool to rt before ether (400 ml) was added. This mixture was then washed with water (2×200 ml), and the mixed aq. layers were further extracted with ether (150 ml). The combined organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/heptane=1/1=>DCM) gave the pure product 3-(3,5-difluoro-4-methyl-phenyl)-acrylic acid butyl ester as a yellow oil which was further dried under HV (4.690 g; 55%). LC-MS: tR=1.10 min.; [M+H]+: no ionisation.

Aufarbeitung

  1. additionwas added
  2. washThis mixture was then washed with water (2×200 ml)
  3. extractionthe mixed aq. layers were further extracted with ether (150 ml)
  4. dry with materialThe combined organic layers were dried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customPurification by FC (DCM/heptane=1/1=>DCM)

Quellen und Nachweise

ORD-Eintrag
ord-482cf023f68c476b9ff7401d21f78deb
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188082B2

Notizen zur Reaktion

Wird geladen…