Pentafluoropyridine → 2,3,5,6-Tetrafluoropyridine

HRID 1353110Notes

Reaction equation

HRID 1353110 reaction equation
[F:1][C:2]1[N:7]=[C:6]([F:8])[C:5]([F:9])=[C:4](F)[C:3]=1[F:11]>[Zn].N>[F:8][C:6]1[C:5]([F:9])=[CH:4][C:3]([F:11])=[C:2]([F:1])[N:7]=1

Participants

4

Reactant 1

HCID 69690Pentafluoropyridine

Product 1

HCID 1377492,3,5,6-TetrafluoropyridineYield 84.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 222AmmoniaSolvent

Procedure

80 g of pentafluoropyridine (Janssen) and 111.5 g of zinc power were added to 560 ml of 20% aqueous ammonia. The resulting mixture was stirred at room temperature for 5 hours, and then gently refluxed to remove water using a Dean-Stark trap, to obtain 60.4 g (yield: 84.5%) of the title compound.

Workup

  1. temperaturegently refluxed
  2. customto remove water using a Dean-Stark trap

Sources & evidence

ORD record
ord-3fb78612de14466d8d0354fdf46a2fe2
Source dataset
uspto-grants-2007_05
Patent number
US07220863B2

Reaction notes

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