Hydrochloric Acid → Ethyl 2-chloro-2-(2,6-difluoro-4-nitrophenyl)ethanoate

HRID 634683

Reaktionsgleichung

Reaktionsgleichung von HRID 634683
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.[Cl:12][CH:13](Cl)[C:14]([O:16][CH2:17][CH3:18])=[O:15].CC(C)([O-])C.[K+].Cl>CN(C=O)C>[Cl:12][CH:13]([C:7]1[C:2]([F:1])=[CH:3][C:4]([N+:9]([O-:11])=[O:10])=[CH:5][C:6]=1[F:8])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10808Ethyl dichloroacetateHCID 752721,3-Difluoro-5-nitrobenzeneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 21260294Ethyl 2-chloro-2-(2,6-difluoro-4-nitrophenyl)ethanoateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

A solution of 3,5-difluoronitrobenzene (20 g,126 mmol) and ethyl dichloroacetate (15.8 ml, 129 mmol) in DMF (60 ml) was added to potassium t-butoxide (31.8 g, 283 mmol) in DMF (500 ml) at −25° C. over 30 minutes. The mixture was stirred for 15 minutes at −25° C. then poured on to a mixture of ice (600 g) and 2M hydrochloric acid (500 ml). The aqueous mixture was extracted with ethyl acetate, the combined extracts were washed with water and sodium hydrogen carbonate solution and dried (MgSO4) and the solvent removed by evaporation to give ethyl 2-chloro-2-(2,6-difluoro-4-nitrophenyl)ethanoate (34 g, 97%).

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with ethyl acetate
  2. washthe combined extracts were washed with water and sodium hydrogen carbonate solution
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-ece5942eccfd41b9b50ac2ce665ab347
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184225B2

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