Nitric Acid → 6-Fluoro-2-methyl-3-nitrobenzoic acid

HRID 706578Notes

Reaction equation

HRID 706578 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[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[C:3]([C:4]([OH:6])=[O:5])=[C:7]([CH3:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 134781322-Fluoro-6-methylbenzoic acid

Product 1

HCID 593345776-Fluoro-2-methyl-3-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-15 °C

Procedure

2-Fluoro-6-methylbenzoic acid (40 g, 0.26 mol) was dissolved in 320 mL of sulfuric acid and chilled to −15° C. To this was added 14 mL of fuming nitric acid in 60 mL of sulfuric acid over a 10 minute period. Once the addition was complete, the mixture was stirred at 0° C. for 1 hour, then poured into ice water, and stirred. The resulting solids were collected and then dissolved in EtOAc, which was washed with water, dried over sodium sulfate and concentrated to 50 g (97%) of the title compound.

Workup

  1. additionOnce the addition
  2. stirringstirred
  3. customThe resulting solids were collected
  4. dissolutiondissolved in EtOAc
  5. washwhich was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to 50 g (97%) of the title compound

Sources & evidence

ORD record
ord-f1c2ceebcd89488ea38b1e329df9b862
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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