Nitric Acid → 1-(2-Fluoro-5-nitrophenyl)propan-1-one

HRID 1186132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186132
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10].[N+:12]([O-])([OH:14])=[O:13].O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[C:8](=[O:11])[CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 962WaterHCID 5793991-(2-Fluorophenyl)propan-1-one

Produkt 1

HCID 179677821-(2-Fluoro-5-nitrophenyl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a solution of the 1-(2-fluoro-phenyl)-propan-1-one (99 mmol) in concentrated sulfuric acid (80 ml) cooled down to −30° C. was added slowly fuming nitric acid (8 ml) over 20 min and the solution was stirred at −30° C. for 15 min. The mixture was slowly poured into a stirred mixture of 200 ml of water and 400 g ice. The aqueous phase was extracted with ethyl acetate, the organic layer was extracted again with water and aqueous NaHCO3 1M. The organic layer was dried over Na2SO4, evaporated and the residue was purified by chromatography on silica using a mixture of heptane and ethylacetate as eluent to afford the pure nitro intermediate J. MS (ISP): m/z=198.1 [M+H]+.

Aufarbeitung

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. extractionthe organic layer was extracted again with water and aqueous NaHCO3 1M
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated
  5. customthe residue was purified by chromatography on silica using
  6. additiona mixture of heptane and ethylacetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-faf3105460d64c498f9d3f9d5dbaa911
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673894B2

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