Ethyl Acetate → 5-Fluoro-1-(4-fluorophenyl)indoline-2,3-dione

HRID 1110882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110882
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.[Al+3].[Cl-].[Cl-].[Cl-].C(OCC)(=O)C>C(Cl)Cl.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[C:15]3[C:16](=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[C:1](=[O:5])[C:2]2=[O:3])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 112411734-Fluoro-N-(4-fluorophenyl)benzenamine

Produkt 1

HCID 133395515-Fluoro-1-(4-fluorophenyl)indoline-2,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Oxalyl chloride (9.62 ml, 0.11 mole) was dissolved in 45 ml CH2Cl2. A solution of di-(4-fluorophenyl)amine (19.7 g, 0.096 mole) in 145 ml CH2Cl2 was added over 15 minutes; the temperature rose from 23° to 28°. After stirring 1 hour, AlCl3 (40.8 g) was added portionwise over 15 minutes; the temperature rose from 20° to 30°, and was kept less than 30° by cooling.. After stirring for 10 minutes, the reaction mixture was added to 250 ml ethyl acetate and 500 ml ice and water (the temperature rose to 30° C.). The aqueous layer was washed 2×250 ml ethyl acetate The organic layers were combined, back-washed 1×400 ml H2O, dried over MgSO4, evaporated to solids and triturated with 100 ml 1:1 ether:hexane to recover title product, 19.9 g, m.p. 180°-190°, tlc Rf 0.55 (1:1 ether;hexane)

Aufarbeitung

  1. customrose from 23° to 28°
  2. customrose from 20° to 30°
  3. customwas kept less than 30°
  4. temperatureby cooling
  5. stirringAfter stirring for 10 minutes
  6. customrose to 30° C.
  7. washThe aqueous layer was washed 2×250 ml ethyl acetate The organic layers
  8. washback-washed 1×400 ml H2O
  9. dry with materialdried over MgSO4
  10. customevaporated to solids
  11. customtriturated with 100 ml 1:1 ether
  12. customhexane to recover title product, 19.9 g, m.p. 180°-190°, tlc Rf 0.55 (1:1 ether;hexane)

Quellen und Nachweise

ORD-Eintrag
ord-30b3e43c48ad4b0ca8c824f0275bc5f1
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977178

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