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

HRID 981362Notes

Reaction equation

HRID 981362 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. It 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. stirringIt is stirred with light petroleum
  9. filtrationthe solid product is filtered off under suction
  10. customdried

Sources & evidence

ORD record
ord-1ccd943e5fec4e56827231dbd6320179
Source dataset
uspto-grants-1991_02
Patent number
US04990661

Reaction notes

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