1,3,5-Trichloro-2,4,6-trifluorobenzene → 1,3,5-Trifluorobenzene

HRID 736963Notes

Reaction equation

HRID 736963 reaction equation
Cl[C:2]1[C:7]([F:8])=[C:6](Cl)[C:5]([F:10])=[C:4](Cl)[C:3]=1[F:12].C([O-])(=O)C.[Na+]>[Pd].O>[F:8][C:7]1[CH:2]=[C:3]([F:12])[CH:4]=[C:5]([F:10])[CH:6]=1

Participants

5

Reactant 2

HCID 675731,3,5-Trichloro-2,4,6-trifluorobenzeneHCID 517045Sodium Acetate

Product 1

HCID 97451,3,5-TrifluorobenzeneYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Palladium on carbon (10%, 410 mg), 100 g of water, 21.8 g of 1,3,5-trichloro-2,4,6-trifluorobenzene and 32.9 g of sodium acetate (4.5 equivalents) were placed in a pressure vessel. After flushing with nitrogen, the pressure vessel was heated to 140° C. and pressurized with 12 bar of hydrogen. A hydrogen pressure of 12 bar was maintained at 140° C. for about 12 hours while stirring vigorously. After cooling to 20-25° C., the pressure vessel was depressurized. The two-phase reaction solution was filtered and the phases were then separated. This gave a yield of 88.2% of 1,3,5-trifluorobenzene.

Workup

  1. customAfter flushing with nitrogen
  2. temperatureA hydrogen pressure of 12 bar was maintained at 140° C. for about 12 hours
  3. temperatureAfter cooling to 20-25° C.
  4. customThe two-phase reaction solution
  5. filtrationwas filtered
  6. customthe phases were then separated

Sources & evidence

ORD record
ord-c4bdb7eec03f462c993e6fd1a1db2208
Source dataset
uspto-grants-2009_09
Patent number
US07595426B2

Reaction notes

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