Benzoic acid, 2,4-difluoro-, ethyl ester → HCID 21873648, Verbindung

HRID 1518013Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518013
C(O[C:4](=[O:16])[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8](F)=[CH:7][C:6]=1[F:15])C.[CH2:17]([O:19]C(=O)C1C=CC(F)=CC=1F)[CH3:18].[N+]([O-])(O)=O.O[S:35](O)(=O)=O>>[F:15][C:6]1[C:5]([CH:4]=[O:16])=[CH:10][C:9]2[NH:11][C:17](=[O:19])[CH2:18][S:35][C:8]=2[CH:7]=1

Komponenten

4

Edukt 3

HCID 2737170Benzoic acid, 2,4-difluoro-, ethyl esterHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoateHCID 71777668Sulfuric acid, mixt. with nitric acid

Produkt 1

HCID 21873648HCID 21873648, VerbindungAusbeute 88 %

Versuchsvorschrift

2,4-Difluoro-5-nitro-benzoic acid ethyl ester. To 2,4-difluoro-benzoic acid ethyl ester (6.4 g, 34 mmol) at 0° C. was added HNO3/H2SO4 (1:1, 10 mL). The resulting solution was allowed to warm to RT and was stirred for 18 h. The reaction mixture was partitioned between H2O and CH2Cl2 (400 mL). The organic layer was washed with brine (200 mL), dried (MgSO4), filtered and concentrated to provide 7.0 g (88%) of the title compound as a white solid. MS (ESI): exact mass calculated for C9H7F2NO4, 231.03; m/z not found. 1H NMR (400 MHz, CDCl3): 8.78 (dd, J=8.3, 7.3, 1H), 7.14 (t, J=9.9, 1H), 4.44 (q, J=7.2, 2H), 1.42 (t, J=7.2, 3H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between H2O and CH2Cl2 (400 mL)
  2. washThe organic layer was washed with brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dcc75de576b244e18478e44a8392f11e
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232391B2

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