Acetic Acid → 2-Fluoro-4-nitrobenzoic acid

HRID 394762Notes

Reaction equation

HRID 394762 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15]C=1C.S(=O)(=O)(O)O.[C:28]([OH:31])(=[O:30])[CH3:29]>O>[F:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:29]=1[C:28]([OH:31])=[O:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 740252-Fluoro-4-nitrotoluene

Product 1

HCID 3026792-Fluoro-4-nitrobenzoic acidYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

[25] To a solution of sodium dichromate (3.87 g, 13 mmol) in acetic acid (20 mL) was added 2-fluoro-4-nitrotoluene (1.55 g, 10 mmol) in portions, followed by dropwise addition of concentrated sulfuric acid (10 g). A strong exotherm was observed (100° C.) and the color changed from orange to green. The reaction was heated at 90° C. for 1 hour and cooled to 25° C. The reaction mixture was dissolved in water (30 mL) and white crystals formed upon cooling at 0° C. The white solid was collected by filtration washed with cold water and dried to give 2-fluoro-4-nitrobenzoic acid (0.99 g, 53%).

Workup

  1. custom(100° C.)
  2. temperaturecooled to 25° C
  3. customwhite crystals formed
  4. temperatureupon cooling at 0° C
  5. filtrationThe white solid was collected by filtration
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-de3ac461e6db41ee91f5228c5701dc7e
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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