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

HRID 2059994Notes

Reaction equation

HRID 2059994 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[CH:10][C:11]=1[CH3:12]>ClCCl>[F:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([OH:13])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27746133-Fluoro-4-methylphenol

Product 1

HCID 127824115-Fluoro-4-methyl-2-nitrophenolYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70% Nitric acid (0.759 mL, 8.42 mmol) was added dropwise to a solution of 3-fluoro-4-methylphenol (966 mg, 7.66 mmol) in dichloromethane (25 mL) at rt. The reaction was stirred for 30 min before being washed with water. The aqueous layer was extracted with dichloromethane (1×) and the combined organics were dried (Na2SO4) and concentrated by rotary evaporation to give a yellow/orange solid. The residue was purified via chromatography (silica, dichloromethane to 0.5% ammonia/9.5% methanol/90% dichloromethane) to give 5-fluoro-4-methyl-2-nitrophenol (D21, 873 mg, 67% yield) as a yellow solid.

Workup

  1. washbefore being washed with water
  2. extractionThe aqueous layer was extracted with dichloromethane (1×)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. concentrationconcentrated by rotary evaporation
  5. customto give a yellow/orange solid
  6. customThe residue was purified via chromatography (silica, dichloromethane to 0.5% ammonia/9.5% methanol/90% dichloromethane)

Sources & evidence

ORD record
ord-1d8aa79f27074e6590a5987e2de20944
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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