Potassium Carbonate → 3-Fluoro-4-nitroaniline

HRID 1964462

Reaktionsgleichung

Reaktionsgleichung von HRID 1964462
[F:1][C:2]1[CH:3]=[C:4]([NH:11]C(=O)C(C)(C)C)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[NH2:11]

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 59129487N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide

Produkt 1

HCID 754013-Fluoro-4-nitroanilineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide (87.0 g, 0.36 mol) in CH2Cl2 (400 mL) and 6N hydrochloric acid (800 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with 1000 mL of ethyl acetate and potassium carbonate (500.0 g) was added portion wise. The aqueous solution was separated and the organic layer was washed with brine and dried over anhydrous Na2SO4. The solvent was removed by evaporation under reduced pressure; the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to afford 3-fluoro-4-nitroaniline (56.0 g, 99%). 1H NMR (300 MHz, CDCl3) δ 8.07 (t, J=8.7 Hz, 1 H), 7.86 (dd, J=2.1, 13.2 Hz 1 H), 7.59 (brs, 2 H), 7.22 (s, 1 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. additionwas added portion wise
  4. customThe aqueous solution was separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f0031b1fb9648f3af9a38b5e89830c5
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415387B2

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