5-Fluoro-2-nitrophenol → Ethyl 2-(5-fluoro-2-nitrophenoxy)propanoate

HRID 901834

Reaktionsgleichung

Reaktionsgleichung von HRID 901834
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[OH:11])([O-:3])=[O:2].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[O:11][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Produkt 1

HCID 19786322Ethyl 2-(5-fluoro-2-nitrophenoxy)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-nitro-5-fluorophenol (1.0 g, 1 eq, 6.36 mmol) and ethyl 2-bromopropionate (0.91 ml, 1.1 eq, 6.99 mmol) in dry acetone (32 ml) was added anhydrous potassium carbonate (2.63 g, 3 eq, 19.08 mmol) and the reaction mixture was refluxed for 16 h. The reaction mixture was filtered through celite and then condensed on rotavapour. The residue was diluted with ethyl acetate and washed with water and brine to yield ethyl 2-(2-nitro-5-fluorophenoxy)propanoate as crude compound (1.6 g, yield 98%), which was used in step (ii).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 16 h
  2. filtrationThe reaction mixture was filtered through celite
  3. customcondensed on rotavapour
  4. washwashed with water and brine

Quellen und Nachweise

ORD-Eintrag
ord-27d8f674a3af46f0ab0bc45109755fb1
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365064B2

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