Nitric Acid → 2,4,5-Trifluoro-3-nitrobenzoic acid

HRID 231997Notes

Reaction equation

HRID 231997 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19]>>[F:1][C:2]1[C:10]([N+:18]([O-:20])=[O:19])=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 5211702,4,5-Trifluorobenzoic acid

Product 1

HCID 226086252,4,5-Trifluoro-3-nitrobenzoic acid

Conditions

Temperature
70 °C

Procedure

3.5 g (0.02 mol) of 2,4,5-trifluorobenzoic acid are introduced into a mixture of 6.8 ml of concentrated sulphuric acid and 8 ml of 98% strength nitric acid at 5°-10° C., and the mixture is then stirred without cooling. The temperature increases to 70° C. The mixture is heated for 5 hours at 80°-90° C., a further 8 ml of 98% strength nitric acid are added, and the mixture is heated at 80° C. for 2 hours. The mixture is then introduced into 100 ml of ice water, extracted thoroughly with dichloromethane, dried using sodium sulphate and concentrated. The oil remaining crystallizes. If is stirred with light petroleum, and the solid product is filtered off under suction and dried.

Workup

  1. temperaturewithout cooling
  2. temperatureThe mixture is heated for 5 hours at 80°-90° C.
  3. temperaturethe mixture is heated at 80° C. for 2 hours
  4. extractionextracted thoroughly with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe oil remaining crystallizes
  8. stirringIf is stirred with light petroleum
  9. filtrationthe solid product is filtered off under suction
  10. customdried

Sources & evidence

ORD record
ord-c6c7c08363404d509cf75ce08f63732f
Source dataset
uspto-grants-1989_07
Patent number
US04851160

Reaction notes

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