Acetic Acid → 3-Fluoro-4-nitrobenzoic acid

HRID 880502Notes

Reaction equation

HRID 880502 reaction equation
[F:1][C:2]1[CH:7]=C(C)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].S(=O)(=O)(O)O.[C:28]([OH:31])(=[O:30])[CH3:29]>>[F:1][C:2]1[CH:7]=[C:29]([CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[C:28]([OH:31])=[O:30]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 24502Potassium DichromateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

Product 1

HCID 2306533-Fluoro-4-nitrobenzoic acidYield 83%

Conditions

Temperature
120 °C

Procedure

2-Fluoro-4-methyl-1-nitro-benzene (1.0 g, 12.9 mmol) was added portion-wise to a suspension of potassium dichromate (5.04 g, 17.16 mmol) in glacial acetic acid (8 mL) follow by concentrated sulfuric acid (3.6 mL). The reaction mixture was heated to 120° C. for 2 h and then allowed to cool to ambient temperature. The reaction was quenched with crushed ice and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-fluoro-4-nitro-benzoic acid (1.9 g, 83%) as a white solid.

Workup

  1. temperatureto cool to ambient temperature
  2. customThe reaction was quenched with crushed ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-da5f8b74d0674364adbf2a1c491402f9
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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