Triethylamine → 3,5-Difluoroaniline

HRID 1609406Notes

Reaction equation

HRID 1609406 reaction equation
Cl[C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[CH:5][C:3]=1[NH2:4].C(N(CC)CC)C.[H][H]>[C].[Pd].O>[F:9][C:8]1[CH:2]=[C:3]([CH:5]=[C:6]([F:10])[CH:7]=1)[NH2:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27364942-Chloro-3,5-difluoroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 965953,5-DifluoroanilineYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 500 ml SUS autoclave, 45.4 g (purity: 98%, 0.272 mol) of 2-chloro-3,5-difluoroaniline, 1.84 g of 5% palladium-carbon, 30.2 g (0.299 mol) of triethylamine and 45.4 g of water were introduced, and hydrogen gas was sealed in. Then, the mixture was reacted under a hydrogen gas pressure of 15 kg/cm2 at a temperature of 100° C. for 4 hours. Then, the reaction solution was cooled to 50° C. Then, palladium-carbon was filtered off, and 50 g of a 25% sodium hydroxide aqueous solution was added. The mixture was stirred and left to stand still. Then, the oil layer was separated. Then, this oil layer was distilled to recover 28.5 g of triethylamine, and then 32.3 g (purity: 99%, yield: 91.0%) of 3,5-difluoroaniline was obtained.

Workup

  1. customThen, the mixture was reacted under a hydrogen gas pressure of 15 kg/cm2 at a temperature of 100° C. for 4 hours
  2. filtrationThen, palladium-carbon was filtered off
  3. addition50 g of a 25% sodium hydroxide aqueous solution was added
  4. waitleft
  5. customThen, the oil layer was separated
  6. distillationThen, this oil layer was distilled
  7. customto recover 28.5 g of triethylamine

Sources & evidence

ORD record
ord-46277cd71d3e4c0e8802999a46e200dd
Source dataset
uspto-grants-1995_03
Patent number
US05399767

Reaction notes

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