Nitric Acid → 1-Nitro-3-(pentafluoroethyl)benzene

HRID 1414508Notes

Reaction equation

HRID 1414508 reaction equation
[F:1][C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([F:7])[C:3]([F:6])([F:5])[F:4].[N+:14]([O-])([OH:16])=[O:15].S(=O)(=O)(O)O>>[N+:14]([C:10]1[CH:9]=[C:8]([C:2]([F:7])([F:1])[C:3]([F:5])([F:4])[F:6])[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11298517(Pentafluoroethyl)Benzene

Product 1

HCID 232334121-Nitro-3-(pentafluoroethyl)benzene

Conditions

Temperature
45 °C

Procedure

74 G. (0.4 moles) of pentafluoroethylbenzene is cooled to 5° C. and treated dropwise with a mixture of 22 g. (0.33 moles) of concentrated nitric acid and 33 g. (0.32 moles) of concentrated sulfuric acid. The temperature is maintained at 5°-15° C. during the 1 hour addition period and then raised to 45° C. for 1 hour. The reaction mixture is cooled and poured onto ice. The aqueous mixture is extracted with ether, the ether extracts washed with water, dried over sodium sulfate, and the residue is distilled at 0.35 mm. of Hg at 74°-75° C. The yield is 84 g. (87%) of m-nitro-pentafluoroethylbenzene.

Workup

  1. additiontreated dropwise with a mixture of 22 g
  2. temperatureThe temperature is maintained at 5°-15° C. during the 1 hour addition period
  3. temperatureThe reaction mixture is cooled
  4. additionpoured onto ice
  5. extractionThe aqueous mixture is extracted with ether
  6. washthe ether extracts washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationthe residue is distilled at 0.35 mm. of Hg at 74°-75° C

Sources & evidence

ORD record
ord-90381090dab340e99c6bd3cef3c8bccc
Source dataset
uspto-grants-1977_01
Patent number
US04001406

Reaction notes

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