Dimethylformamide → 6-Chloro-5-fluoropyridine-3-carbaldehyde

HRID 2066862

Reaktionsgleichung

Reaktionsgleichung von HRID 2066862
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([F:14])[C:10]([Cl:13])=[N:11][CH:12]=1.CN([CH:18]=[O:19])C.CCOC(C)=O>CCOCC>[Cl:13][C:10]1[N:11]=[CH:12][C:7]([CH:18]=[O:19])=[CH:8][C:9]=1[F:14]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 27632855-Bromo-2-chloro-3-fluoropyridineHCID 178418339Butyllithium

Produkt 1

HCID 216981946-Chloro-5-fluoropyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Butyl lithium (2.5 M in hexane, 2.5 mL, 6.3 mmol) was added to 5-bromo-2-chloro-3-fluoro-pyridine (1 g, 4.75 mmol) in 10 mL of ether at −78° C. After 10 minutes, DMF (5 mL) was added and the mixture was warmed to room temperature over 1 h. The mixture was poured into 20 mL of EtOAc and the mixture was washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate and concentrated to afford the crude 53a (0.92 g) as a brown oil: LC-MS160.0 (MH+).

Aufarbeitung

  1. washthe mixture was washed with water (20 mL) and brine (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c4d725c0dae449cf9394add94b98aae3
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293729B2

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