Réaction #7592

Équation de réaction

5-benzyloxy-2-fluoro-4-methylnitrobenzene

→

5-benzyloxy-2-fluoro-4-methylaniline

Rendement 87.7%

Solvants

acetic acid

water

Conditions de réaction

Traitement

1. 1
   Autreat ambient temperature
2. 2
   TempératureThe mixture was heated
3. 3
   Températureit was cooled
4. 4
   Autrepartitioned between ethyl acetate and water
5. 5
   LavageThe organic layer was washed with water, aqueous saturated sodium carbonate solution
6. 6
   Séchagebrine, dried (MgSO4)
7. 7
   Autrethe solvent evaporated
8. 8
   AutreThe residue was purified by flash chromatography

Mode opératoire

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%).

Source