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

HRID 1968949Notes

Reaction equation

HRID 1968949 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-2e55774e2bdc432fbc935968c12ac8f5
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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