Acetic Acid → 2-Fluoro-4-nitrobenzoic acid

HRID 507484Notes

Reaction equation

HRID 507484 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 0C. 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. filtrationThe white solid was collected by filtration
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-8fe2ef6cb6b34788a0fc8a352ff0911e
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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