Dichloromethane → N,N,4-Triethyl-2-fluorobenzamide

HRID 2100612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100612
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([Zn]CC)[CH3:23].ClCCl>CN(C=O)C.C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:9]([N:8]([CH2:11][CH3:12])[C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([CH2:22][CH3:23])=[CH:3][C:4]=1[F:15])[CH3:10]

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 246940264-Bromo-N,N-diethyl-2-fluorobenzamideHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 69055558N,N,4-Triethyl-2-fluorobenzamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 4-bromo-N,N-diethyl-2-fluorobenzamide (5.12 g, 18.9 mmol) in 100 mL of DMF was added potassium carbonate (6.45 g, 46.7 mmol) and diethylzinc (25.5 mL of a 1.1 M solution in toluene, 28.02 mmol). The solution was degassed with a stream of argon and then there was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (305 mg, 0.37 mmol). The reaction mixture was allowed to stir at 80° C. for 3 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate. The organics were washed with water and brine, dried (MgSO4) and concentrated. The residue was purified (ISCO, elution with 0-40% EtOAc/hexane, 40 min) to afford 3.70 g (88%) of the title compound as a colorless oil. LRMS (ESI): 224.2 (M+H)+.

Aufarbeitung

  1. customThe solution was degassed with a stream of argon
  2. temperatureto cool
  3. washThe organics were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified
  7. wash(ISCO, elution with 0-40% EtOAc/hexane, 40 min)

Quellen und Nachweise

ORD-Eintrag
ord-95297d6ca93c47a59f8ec56740b21ebb
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572805B2

Notizen zur Reaktion

Wird geladen…