Potassium Nitrate → 2-chloro-3-nitro-5-(trifluoromethyl)benzoic Acid

HRID 1367941Notes

Reaction equation

HRID 1367941 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:15]([O-])([O-:17])=[O:16].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 100844572-chloro-3-nitro-5-(trifluoromethyl)benzoic AcidYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a stirring solution of 4.48 g (20 mmol) of 2-chloro-5-trifluoromethyl-benzoic acid suspended in 40 mL of conc. H2SO4 at −20° C. was added dropwise a cold solution of 1.05 eq of potassium nitrate dissolved in 12 mL of sulfuric acid. The reaction mixture was stirred −20° C. for 15 min then warmed up to r.t. overnight. The mixture was poured into a beaker containing ice. The resulting solid was collected, washed with cold water and dried to give 4.8 g (90%) of 2-chloro-3-nitro-5-trifluoromethyl-benzoic acid as a solid. LCMS: 270 (M+1)+.

Workup

  1. temperaturethen warmed up to r.t. overnight
  2. additionThe mixture was poured into a beaker
  3. additioncontaining ice
  4. customThe resulting solid was collected
  5. washwashed with cold water
  6. customdried

Sources & evidence

ORD record
ord-f66d79d872c740e995d0e7e98b86e966
Source dataset
uspto-grants-2011_02
Patent number
US07893267B2

Reaction notes

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