Reaction #7577

Reaction equation

sodium hydroxide

4-fluoro-2-methyl-5-nitrophenol

→

2-fluoro-5-hydroxy-4-methylaniline

Yield 47.0%

Solvents

water

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureat reflux for 4 hours
3. 3
   Temperatureto cool
4. 4
   Extractionextracted with ethyl acetate (100 ml)
5. 5
   ExtractionThe ethyl acetate extract
6. 6
   Dryingwas dried (MgSO4)
7. 7
   Otherthe solvent removed by evaporation

Procedure

A mixture of 4-fluoro-2-methyl-5-nitrophenol (2.1 g, 13 mmol), iron powder (1 g, 18 mmol) and iron(II)sulphate (1.5 g, 10 mmol) in water (40 ml) was heated at reflux for 4 hours. The reaction mixture was allowed to cool, neutralised with 2M aqueous sodium hydroxide solution and extracted with ethyl acetate (100 ml). The ethyl acetate extract was dried (MgSO4) and the solvent removed by evaporation to give 2-fluoro-5-hydroxy-4-methylaniline (0.8 g, 47%) as a solid.

Source