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

HRID 1985747Notes

Reaction equation

HRID 1985747 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 an additional 16 h. The homogeneous mixture was poured onto 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 onto 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-6b751700459148b7806203d325fd60bf
Source dataset
uspto-grants-2009_06
Patent number
US07547711B2

Reaction notes

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