HCID 135702939, compound → 4-Amino-2,5-difluorophenol

HRID 900512Notes

Reaction equation

HRID 900512 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]=NC2C=CC=CC=2)[C:5]([F:16])=[CH:4][C:3]=1[OH:17]>C(O)C.[Pd]>[NH2:8][C:6]1[C:5]([F:16])=[CH:4][C:3]([OH:17])=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 135702939HCID 135702939, compound

Product 1

HCID 27787624-Amino-2,5-difluorophenolYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

42 g (0.18 mol) of 2,5-difluoro-4-(phenyidiazenyl)phenol from Example 5 and 1 g of Pd/C (10%) were initially charged in 650 ml of ethanol. The solution was degassed and aerated with hydrogen. The mixture was stirred at room temperature under a 1 bar hydrogen atmosphere for 18 hours. On completion of hydrogen uptake, the catalyst was filtered off and the filtrate distilled under reduced pressure, and dried under high vacuum at 70° C. for 4 hours. The residue (24 g) was recrystallized from ethanol and dried. 15 g (60%) of 4-amino-2,5-difluorophenol are obtained as orange-brown powder.

Workup

  1. customThe solution was degassed
  2. filtrationOn completion of hydrogen uptake, the catalyst was filtered off
  3. distillationthe filtrate distilled under reduced pressure
  4. customdried under high vacuum at 70° C. for 4 hours
  5. customThe residue (24 g) was recrystallized from ethanol
  6. customdried

Sources & evidence

ORD record
ord-b527febc0e914fa891bde9b373399540
Source dataset
uspto-grants-2008_04
Patent number
US07358397B2

Reaction notes

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