Réaction #7576

Équation de réaction

nitric acid

4-fluoro-2-methylphenyl methyl carbonate

→

4-fluoro-2-methyl-5-nitrophenol

Rendement 22.0%

Solvants

sulphuric acid

sulphuric acid

Conditions de réaction

Traitement

1. 1
   Autrewas kept below 50° C
2. 2
   Filtrationthe precipitated product collected by filtration
3. 3
   AutreThe crude product was purified by chromatography on silica eluting with methylene chloride/hexane progressing
4. 4
   Températurethrough increasingly polar mixtures to methanol/methylene chloride (1/19)

Mode opératoire

A mixture of concentrated nitric acid (6 ml) and concentrated sulphuric acid (6 ml) was added slowly to a solution of 4-fluoro-2-methylphenyl methyl carbonate (11.34 g, 62 mmol) in concentrated sulphuric acid (6 ml) such that the temperature of the reaction mixture was kept below 50° C. The mixture was stirred for 2 hours, then ice/water was added and the precipitated product collected by filtration. The crude product was purified by chromatography on silica eluting with methylene chloride/hexane progressing through increasingly polar mixtures to methanol/methylene chloride (1/19) to give 4-fluoro-2-methyl-5-nitrophenol (2.5 g, 22%) as a solid.

Source