4,5-difluoro-2-hydroxy-n,n-dimethylbenzylamine → 4,5-DIFLUORO-2-METHYLPHENOL

HRID 1071217Notes

Reaction equation

HRID 1071217 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:5]([CH2:6]N(C)C)=[C:4]([OH:13])[CH:3]=1.[H][H]>C(O)(=O)C.[Pd]>[F:12][C:11]1[C:2]([F:1])=[CH:3][C:4]([OH:13])=[C:5]([CH3:6])[CH:10]=1

Participants

5

Reactant 2

HCID 102415484,5-difluoro-2-hydroxy-n,n-dimethylbenzylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 121472874,5-DIFLUORO-2-METHYLPHENOL

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

214 g of 4,5-difluoro-2-hydroxy-N,N-dimethylbenzylamine are initially charged in 700 ml of acetic acid in an autoclave, admixed with 50 g of palladium/activated carbon (5%) and heated with 70 bar of hydrogen to 100° C. for 26 hours. The autoclave is cooled and decompressed. The catalyst is filtered off and washed with acetic acid, and the filtrate is admixed with 3 000 ml of water. This aqueous solution is extracted three times with methyl tert-butyl ether. The combined organic phases are washed once with water and dried, and the solvent is distilled off under reduced pressure. The crude product is fractionally distilled under reduced pressure. The distillate can be further purified by crystallization. 98 g (58% of theory) of a colourless solid are obtained having a melting point of 68-70° C. and a boiling point of 78-80° C. at 13 mbar.

Workup

  1. temperatureThe autoclave is cooled
  2. filtrationThe catalyst is filtered off
  3. washwashed with acetic acid
  4. extractionThis aqueous solution is extracted three times with methyl tert-butyl ether
  5. washThe combined organic phases are washed once with water
  6. customdried
  7. distillationthe solvent is distilled off under reduced pressure
  8. distillationThe crude product is fractionally distilled under reduced pressure
  9. distillationThe distillate can be further purified by crystallization
  10. custom98 g (58% of theory) of a colourless solid are obtained

Sources & evidence

ORD record
ord-053a654ce0bc447f820ca57ce90e8b3e
Source dataset
uspto-grants-2005_06
Patent number
US06903239B2

Reaction notes

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