Acetic Acid → 2,3,5-Trifluoropyridine

HRID 1353112Notes

Reaction equation

HRID 1353112 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4](NN)[N:3]=1.C(O)(=O)C>S([O-])([O-])(=O)=O.[Cu+2].O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21551824(3,5,6-Trifluoro-2-pyridyl)hydrazine

Product 1

HCID 27832872,3,5-TrifluoropyridineYield 87.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

8.2 g of the compound obtained in Step 2 was added to a mixture of 320 ml of acetic acid and 120 ml of water, and 400 ml of 10% aqueous copper sulfate was added thereto. The resulting mixture was refluxed for 24 hours while removing water using a Dean-Stark trap, and the residue was dried to obtain 5.8 g (yield: 87.1%) of the title compound.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was refluxed for 24 hours
  3. customwhile removing water using a Dean-Stark trap
  4. customthe residue was dried

Sources & evidence

ORD record
ord-b4f9b248009242ea8d9fc2788ae70a7d
Source dataset
uspto-grants-2007_05
Patent number
US07220863B2

Reaction notes

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