Nitric Acid → 2,4-Difluoro-5-nitrobenzoic acid

HRID 966150Notes

Reaction equation

HRID 966150 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 741022,4-Difluorobenzoic acid

Product 1

HCID 27828222,4-Difluoro-5-nitrobenzoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of 2,4-difluorobenzoic acid (9.985 g, 63.2 mmol) in concentrated sulfuric acid (30 mL) at 0° C. was added fuming nitric acid (30 mL) over 30 min. The mixture was allowed to warm to RT and stirred for additional 16 h. The homogeneous mixture was poured over ice and extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated in vacuo to afford 2,4-difluoro-5-nitrobenzoic acid (12.56 gm, 98%) as pale yellow solid.

Workup

  1. additionThe homogeneous mixture was poured over ice
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8b4dfddcfec46ffa19a9b2cc989b2b4
Source dataset
uspto-grants-2005_10
Patent number
US06951859B2

Reaction notes

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