Nitric Acid → 4-Fluoro-2-methyl-5-nitrophenol

Participants

Reaction Steps

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. 1H NMR Spectrum: (DMSOd6; CD3COOD) 2.31(s, 3H), 7.38(d, 1H) ,7.58(d, 1H) MS-ESI: 171 [MH]+

Provenance & Evidence