3-Chloro-2,4,5,6-tetrafluoropyridine → 3-Chloro-2,5,6-trifluoropyridine

HRID 1353115Notes

Reaction equation

HRID 1353115 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[N:4][C:5]([F:10])=[C:6]([F:9])[C:7]=1F>[Zn].N>[Cl:1][C:2]1[C:3]([F:11])=[N:4][C:5]([F:10])=[C:6]([F:9])[CH:7]=1

Participants

4

Reactant 1

HCID 1371833-Chloro-2,4,5,6-tetrafluoropyridine

Product 1

HCID 27832523-Chloro-2,5,6-trifluoropyridineYield 92.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 222AmmoniaSolvent

Procedure

55.5 g of 3-chloro-2,4,5,6-tetrafluoropyridine (Fluorochem) and 20 g of zinc powder were added to 560 ml of 20% aqueous ammonia, and the resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was refluxed while removing water using a Dean-Stark trap, to obtain 46.2 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed
  2. customwhile removing water using a Dean-Stark trap

Sources & evidence

ORD record
ord-e5e73a76a7c440f0b2612e2497c1cd0d
Source dataset
uspto-grants-2007_05
Patent number
US07220863B2

Reaction notes

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