Acetic Acid → 5-Chloro-2,3-difluoropyridine

HRID 1353117Notes

Reaction equation

HRID 1353117 reaction equation
[Cl:1][C:2]1[C:3](NN)=[N:4][C:5]([F:9])=[C:6]([F:8])[CH:7]=1.C(O)(=O)C>S([O-])([O-])(=O)=O.[Cu+2].O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([F:9])=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 21102306HCID 21102306, compound

Product 1

HCID 27832485-Chloro-2,3-difluoropyridineYield 86.5%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Procedure

17.9 g of the compound obtained in Step 2 was added to a mixture of 360 ml of acetic acid and 135 ml of water, and 450 ml of 10% aqueous copper sulfate was added dropwise thereto. The resulting mixture was refluxed for 24 hours while removing water using a Dean-Stark trap, to obtain 12.9 g of the title compound.

Workup

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

Sources & evidence

ORD record
ord-6785ea2635d9448d861381c92336438c
Source dataset
uspto-grants-2007_05
Patent number
US07220863B2

Reaction notes

Loading…