Ethanol → 1-[4-Fluoro-2-(methylamino)phenyl]ethanone

HRID 1085916

Reaktionsgleichung

Reaktionsgleichung von HRID 1085916
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9]S(C)=O)=[C:4]([NH:14][CH3:15])[CH:3]=1.C(O)C>C(O)(=O)C.[Zn]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH3:9])=[C:4]([NH:14][CH3:15])[CH:3]=1

Komponenten

5

Edukt 2

HCID 702EthanolHCID 10059700Ethanone, 1-[4-fluoro-2-(methylamino)phenyl]-2-(methylsulfinyl)-

Produkt 1

HCID 199784601-[4-Fluoro-2-(methylamino)phenyl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

A solution of 1-(4-fluoro-2-methylaminophenyl)-2-methylsulphinylethanone (161.0 g), prepared in a similar manner to that described in Example 1, in acetic acid (770 ml) was added to a stirred mixture of zinc dust (228.2 g), acetic acid (210 ml) and ethanol (392 ml) at 80° over 1 hour. The mixture was stirred at 80° for a further 2 hours and then allowed to cool to ambient temperature. The combined filtrates obtained after filtration and washing the residue with dichloromethane (400 ml) were concentrated by distillation until the temperature of the remaining mixture reached 132° and then cooled to ambient temperature. Water (1 1) and dichloromethane (330 ml) were added sequentially, the mixture stirred for 10 minutes and the layers then separated. The aqueous phase was extracted with further dichloromethane (2×200ml), the organic extracts combined, then washed with aqueous sodium hydroxide solution (5M; 200 ml) and evaporated in vacuo. Distillation in vacuo (b.p. 74°, 0.4 mm Hg) of the residue gave 4'-fluoro-2'-(methylamino)acetophenone, m.p. 52°-53°.

Aufarbeitung

  1. customThe combined filtrates obtained
  2. filtrationafter filtration
  3. washwashing the residue with dichloromethane (400 ml)
  4. concentrationwere concentrated by distillation until the temperature of the remaining mixture
  5. customreached 132°
  6. temperaturecooled to ambient temperature
  7. additionWater (1 1) and dichloromethane (330 ml) were added sequentially
  8. stirringthe mixture stirred for 10 minutes
  9. customthe layers then separated
  10. extractionThe aqueous phase was extracted with further dichloromethane (2×200ml)
  11. washwashed with aqueous sodium hydroxide solution (5M; 200 ml)
  12. customevaporated in vacuo
  13. distillationDistillation in vacuo (b.p. 74°, 0.4 mm Hg) of the residue

Quellen und Nachweise

ORD-Eintrag
ord-46d1d858bed74796b531d3ac63c5ba25
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05011931

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