N-(4-fluorophenyl)acetamide → 4-Fluoro-N-(4-fluorophenyl)benzenamine

HRID 1723553

Reaktionsgleichung

Reaktionsgleichung von HRID 1723553
[F:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7](=O)[CH3:8])=[CH:4][CH:3]=1.BrC1C=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN1CCCC1=O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([NH:6][C:7]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:8]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 9601N-(4-fluorophenyl)acetamideHCID 99931-Bromo-4-fluorobenzeneHCID 11430Potassium Carbonate

Produkt 1

HCID 112411734-Fluoro-N-(4-fluorophenyl)benzenamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of p-fluoroacetanilide (76.5 g, 0.5 mole), 4-bromofluorobenzene (262.5 g, 1.5 mole), K2CO3 (76 g, 0.55 mole), Cu2Br2 (157.8 g, 0.55 mole) and N-methylpyrrolidone (600 ml) were heated at 175°-180°. After allowing low boiling material to condense off, the mixture was heated at reflux for 7 days. The mixture was cooled to 60° and quenched into a mixture of 2 liters H2O, 600 ml ethylenediamine and 1.2 liters toluene, filtered and the toluene layer separated, back-washed 2×600 ml H2O, treated with activated carbon, dried over MgSO4 and concentrated to oily solids in vacuo. The latter were taken up in 1.5 liters 10% ethanolic KOH, refluxed 18 hours and concentrated in vacuo to an oil. The oil was partitioned between 750 ml H2O and 750 ml. ether. The water layer was washed 2× 200 ml ether. The organic layers were combined, back-washed 2×200 ml H2O, treated with activated carbon, dried over MgSO4, reconcentrated to an oil (60.3 g) and distilled to yield purified title product 41.6 g, b.p. 158°-160°/2 mm.

Aufarbeitung

  1. temperaturewere heated at 175°-180°
  2. customto condense off, the mixture
  3. temperaturewas heated
  4. temperatureat reflux for 7 days
  5. temperatureThe mixture was cooled to 60°
  6. customquenched into a mixture of 2 liters H2O, 600 ml ethylenediamine and 1.2 liters toluene
  7. filtrationfiltered
  8. customthe toluene layer separated
  9. washback-washed 2×600 ml H2O
  10. additiontreated with activated carbon
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated to oily solids in vacuo
  13. temperaturerefluxed 18 hours
  14. concentrationconcentrated in vacuo to an oil
  15. customThe oil was partitioned between 750 ml H2O and 750 ml
  16. washThe water layer was washed 2× 200 ml ether
  17. washback-washed 2×200 ml H2O
  18. additiontreated with activated carbon
  19. dry with materialdried over MgSO4
  20. distillationdistilled
  21. customto yield
  22. custompurified title product 41.6 g, b.p. 158°-160°/2 mm

Quellen und Nachweise

ORD-Eintrag
ord-e45b1f0b1de34d9fb681a94d2dc2e4cb
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04861880

Verknüpfte Notizen

Wird geladen…