Potassium Nitrate → 2,3,6-Trifluoro-5-nitrobenzoic acid

HRID 2107588Notes

Reaction equation

HRID 2107588 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([OH:6])=[O:5].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[F:12][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[CH:9][C:10]([F:11])=[C:2]([F:1])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 5200622,3,6-Trifluorobenzoic acid

Product 1

HCID 156318282,3,6-Trifluoro-5-nitrobenzoic acidYield 83.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

2,3,6-Trifluorobenzoic acid (21.0 g) is added to conc. sulfuric acid (120 ml) under ice-cooling. To the mixture is added dropwise a solution of potassium nitrate (14.5 g) in conc sulfuric acid (30 ml) at below 20° C. After the addition, the mixture is stirred at room temperature for one hour. The reaction mixture is poured into ice water and extracted with diethyl ether. The extract is dried over magnesium sulfate, and then the solvent is distilled off. The residue is recrystallized from dichloromethane-n-hexane to give 2,5,6-trifluoro-3-nitrobenzoic acid (22 g), as colorless prisms, m.p. 98°-99° C.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. extractionextracted with diethyl ether
  4. dry with materialThe extract is dried over magnesium sulfate
  5. distillationthe solvent is distilled off
  6. customThe residue is recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-18c0f17dddf24c698bf0cdca4385e1c1
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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