Fluorobenzene → (4-Fluorophenyl)(pyridin-3-yl)methanone

HRID 568080

Reaktionsgleichung

Reaktionsgleichung von HRID 568080
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].[OH-].[Na+].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=2)=[O:9])=[CH:20][CH:19]=1

Komponenten

5

Edukt 4

HCID 10008FluorobenzeneHCID 14798Sodium HydroxideHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 762660(4-Fluorophenyl)(pyridin-3-yl)methanone

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 140 g of nicotinic acid chloride hydrochloride in 500 ml of fluorobenzene cooled to 0° C. are added 280 g of aluminium chloride portionwise. The mixture is held under reflux for 6 hours, cooled and then poured onto ice. After the addition of sodium hydroxide up to pH=8, the mixture is extracted with dichloromethane. The organic phase is dried over magnesium sulphate and then evaporated under vacuum. The residue crystallises in a pentane/diisopropyl ether mixture giving 108.5 g of 3-(4-fluorobenzoyl)pyridine in the form of crystals melting at 91° C.

Aufarbeitung

  1. temperatureunder reflux for 6 hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. extractionthe mixture is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated under vacuum
  7. customThe residue crystallises in a pentane/diisopropyl ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-ffe533d9ce28413ca8cbdc337e853fb3
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180651B2

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