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

HRID 550346Notes

Reaction equation

HRID 550346 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].S(=O)(=O)(O)O.[N+:20]([O-])([OH:22])=[O:21]>>[Cl:1][C:2]1[C:10]([N+:20]([O-:22])=[O:21])=[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 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 100844572-chloro-3-nitro-5-(trifluoromethyl)benzoic Acid

Procedure

After dissolving at room temperature 2-chloro-5-trifluoromethylbenzoic acid (2.25 g; 10 mmol) in fuming sulfuric acid comprising 20% oleum (6 ml), fuming nitric acid (1.7 ml) is added dropwise over 30 minutes, so as to maintain the temperature of the reaction medium below 60° C. After cooling, ice is added and the precipitate is separated out, washed with water and dried. After recrystallisation from water, 2.15 g of solid corresponding to 2-chloro-3-nitro-5-trifluoromethylbenzoic acid are obtained (m.p.=173° C.).

Workup

  1. additionis added dropwise over 30 minutes
  2. temperatureso as to maintain the temperature of the reaction medium below 60° C
  3. temperatureAfter cooling
  4. additionice is added
  5. customthe precipitate is separated out
  6. washwashed with water
  7. customdried
  8. customAfter recrystallisation from water, 2.15 g of solid corresponding to 2-chloro-3-nitro-5-trifluoromethylbenzoic acid
  9. customare obtained (m.p.=173° C.)

Sources & evidence

ORD record
ord-4cc06b17f3194de3a35b3de3f9df10a4
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

Loading…