Methanol → Methyl 2-chloro-5-fluoronicotinate

HRID 660239Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660239
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Komponenten

5

Edukt 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 114352432-Chloro-5-fluoronicotinic acid

Produkt 1

HCID 24229209Methyl 2-chloro-5-fluoronicotinateAusbeute 25 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-chloro-5-fluoronicotinic acid (5.2 g, 30 mmol) in methanol (20 ml) was added cone, sulfuric acid (0.5 ml) and the reaction mixture was stirred at reflux for 30 hours. The reaction mixture was cooled to 0° C. and 0.5 N sodium hydroxide solution was added to the mixture. The whole was extracted with diethylether. The organic phase was washed with brine, dried (sodium sulfate), and concentrated to afford 3.2 g (25%) of the title compound:

Aufarbeitung

  1. temperatureat reflux for 30 hours
  2. extractionThe whole was extracted with diethylether
  3. washThe organic phase was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a769b96ebc704cbe967caff54181e0ee
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084476B2

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