Sodium Hydroxide → 1,3,5-Trifluorobenzene

HRID 736964Notes

Reaction equation

HRID 736964 reaction equation
[OH-].[Na+].Cl[C:4]1[C:9]([F:10])=[C:8](Cl)[C:7]([F:12])=[C:6](Cl)[C:5]=1[F:14]>[Pd].O>[F:10][C:9]1[CH:4]=[C:5]([F:14])[CH:6]=[C:7]([F:12])[CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 675731,3,5-Trichloro-2,4,6-trifluorobenzene

Product 1

HCID 97451,3,5-TrifluorobenzeneYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

Palladium on carbon (10%, 300 mg), aqueous sodium hydroxide solution (35% strength, 26.5 g, 232 mmol, 3.7 equivalents), 62 g of water and 1,3,5-trichloro-2,4,6-trifluorobenzene (15 g, 62 mmol) were placed in a pressure vessel. After flushing with nitrogen, the pressure vessel was heated to 140° C. and pressurized with 30 bar of hydrogen. A hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours. After cooling to 20-25° C., the pressure vessel was depressurized. The reaction solution was subjected to an azeotropic distillation via a distillation attachment; the distillate went over at a temperature of 99.5° C. After separation of the phases, the lower organic phase comprised the title compound. Washing with water and drying gave 8.05 g of 1,3,5-trifluorobenzene (98% of theory).

Workup

  1. customAfter flushing with nitrogen
  2. temperatureA hydrogen pressure of 30 bar was maintained at 140° C. for 12 hours
  3. temperatureAfter cooling to 20-25° C.
  4. distillationThe reaction solution was subjected to an azeotropic distillation via a distillation attachment
  5. customwent over at a temperature of 99.5° C
  6. customAfter separation of the phases
  7. washWashing with water
  8. customdrying

Sources & evidence

ORD record
ord-0ab5e9897d1e45df9c7046294558eb20
Source dataset
uspto-grants-2009_09
Patent number
US07595426B2

Reaction notes

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