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Ethyl bromoacetate → Ethyl 2-(5-fluoro-2-nitrophenoxy)acetate

HRID 247772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 247772
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:7]=1)[O:8][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Produkt 1

HCID 13752803Ethyl 2-(5-fluoro-2-nitrophenoxy)acetateAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture consisting of 5-fluoro-2-nitrophenol (47.1 g), acetonitrile (300 ml) and potassium carbonate (46 g) was added ethyl bromoacetate (60.1 g) dropwise at a temperature from 50° to 60° C., followed by a five-hour refluxing under heating and then filtration under cooling. The resulting filtrate was subjected to distillation under reduced pressure, and then dissolved in toluene (350 ml). The resulting toluene solution was washed with water, a 5% aqueous solution of potassium hydroxide, and water, in that order, followed by drying with magnesium sulfate and the toluene was distilled off therefrom under reduced pressure. The residue was distilled under reduced pressure to collect a fraction boiling at from 154° to 156° C., so as to obtain ethyl 5-fluoro-2-nitrophenoxyacetate (65.3 g). The whole quantity of the reaction product was dissolved in ethanol (8.1 l), followed by addition thereto of a solution of ammonium chloride (60 g) and water (400 ml). To the resulting mixture was added zinc dust (60.5 g) portionwise at a temperature of from 20° to 30° C.

Aufarbeitung

  1. waitfollowed by a five-hour
  2. temperaturerefluxing
  3. temperatureunder heating
  4. filtrationfiltration
  5. temperatureunder cooling
  6. distillationThe resulting filtrate was subjected to distillation under reduced pressure
  7. dissolutiondissolved in toluene (350 ml)
  8. washThe resulting toluene solution was washed with water
  9. dry with materialby drying with magnesium sulfate
  10. distillationthe toluene was distilled off
  11. distillationThe residue was distilled under reduced pressure
  12. customto collect a fraction
  13. customboiling at from 154° to 156° C.

Quellen und Nachweise

ORD-Eintrag
ord-dc388e3085664314a2d3ace37e34c634
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05207818

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