Reaktion #7592

Reaktionsgleichung

5-benzyloxy-2-fluoro-4-methylnitrobenzene

→

5-benzyloxy-2-fluoro-4-methylaniline

Ausbeute 87.7%

Lösungsmittel

acetic acid

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat ambient temperature
2. 2
   TemperaturThe mixture was heated
3. 3
   Temperaturit was cooled
4. 4
   Sonstigepartitioned between ethyl acetate and water
5. 5
   WaschenThe organic layer was washed with water, aqueous saturated sodium carbonate solution
6. 6
   Trocknenbrine, dried (MgSO4)
7. 7
   Sonstigethe solvent evaporated
8. 8
   SonstigeThe residue was purified by flash chromatography

Vorschrift

The starting material, 5-benzyloxy-2-fluoro-4-methylaniline, was obtained by adding iron powder (2.88 g, 51 mmol), in portions, to a solution of 5-benzyloxy-2-fluoro-4-methylnitrobenzene (4.8 g, 18 mmol) in acetic acid (33 ml) and water (5.7 ml), at ambient temperature. The mixture was heated and after stirring at 100° C. for 10 minutes, it was cooled and partitioned between ethyl acetate and water. The organic layer was washed with water, aqueous saturated sodium carbonate solution and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using petroleum ether/ethyl acetate (8/2) as eluent to give 5-benzyloxy-2-fluoro-4-methylaniline (3.65 g, 87%).

Quelle