Reaktion #45799

Reaktionsgleichung

Methyl 5-bromo-4-fluoro-2-methoxy-3-nitrobenzoate

→

compound

Ausbeute 88.0%

Methyl 3-amino-5-bromo-4-fluoro-2-methoxybenzoate

Ausbeute 88.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Sonstigethe insoluble matter was separated by filtration
3. 3
   Waschenwith washing with ethyl acetate
4. 4
   SonstigeThe organic layer of the filtrate was evaporated under reduced pressure
5. 5
   WaschenThe organic layer was washed with saturated brine
6. 6
   Trocknendried over anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was evaporated away
8. 8
   Sonstigethe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

Vorschrift

Methyl 5-bromo-4-fluoro-2-methoxy-3-nitrobenzoate (I-229) (1.0 g, 3.25 mmol) was dissolved in acetic acid (10 ml), and at room temperature, iron powder (544 mg, 9.74 mmol) was added, followed by stirring at 130° C. for 4 hours. After cooling to room temperature, the insoluble matter was separated by filtration with washing with ethyl acetate. The organic layer of the filtrate was evaporated under reduced pressure, and the resulting residue was fractionated with ethyl acetate and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (798 mg, 88%) as a colorless gel substance.

Quelle