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

HRID 7480Notes

Reaction equation

HRID 7480 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(=O)(OC)[O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[CH3:14]>S(=O)(=O)(O)O>[F:13][C:10]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:12][C:7]([OH:6])=[C:8]([CH3:14])[CH:9]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 106790444-Fluoro-2-methylphenyl Methoxyformate

Product 1

HCID 108210594-Fluoro-2-methyl-5-nitrophenolYield 22%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-98bc7af75928421daa9e6bde92612e3d
Source dataset
uspto-grants-2006_08
Patent number
US07087602B2

Reaction notes

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