Reaktion #68390

ord-c474b033b567489bbfa0e0a712e1b26f

Reaktionsgleichung

O=C(O)c1ccc(F)c([N+](=O)[O-])c1
4-fluoro-3-nitrobenzoic acid
O=S(=O)(O)O
H2SO4
CCO
EtOH
O=C([O-])O.[Na+]
NaHCO3
O=S(=O)([O-])[O-].[Mg+2]
MgSO4
→
CCOC(=O)c1ccc(F)c([N+](=O)[O-])c1
title compound
CCOC(=O)c1ccc(F)c([N+](=O)[O-])c1
Ethyl 4-Fluoro-3-nitrobenzoate

Edukte

O=C(O)c1ccc(F)c([N+](=O)[O-])c1
4-fluoro-3-nitrobenzoic acid
O=S(=O)(O)O
H2SO4
CCO
EtOH
O=C([O-])O.[Na+]
NaHCO3
O=S(=O)([O-])[O-].[Mg+2]
MgSO4

Reagenzien

Keine

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe suspension was filtered
  2. 2
    Einengenconcentrated in vacuo
  3. 3
    SonstigeThe residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes)

Vorschrift

A solution of 4-fluoro-3-nitrobenzoic acid (Alfa Aesar, 10.0 g, 54 mmol) and concentrated H2SO4 (0.2 ml, 4.1 mmol) in EtOH (200 ml) was refluxed for 40 h. The mixture was cooled to 0° C., solid NaHCO3 and MgSO4 was added, and the suspension was filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→30% EtOAc-hexanes) to yield the title compound as an off-white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524917B2uspto-grants-2013_09