2,3-Difluoro-4-(2-phenyldiazenyl)phenol → 4-Amino-2,3-difluorophenol

HRID 900511Notes

Reaction equation

HRID 900511 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([N:9]=NC2C=CC=CC=2)[CH:5]=[CH:4][C:3]=1[OH:17]>C(O)C.[Pd]>[NH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:17])=[C:2]([F:1])[C:7]=1[F:8]

Participants

4

Reactant 1

HCID 1355741042,3-Difluoro-4-(2-phenyldiazenyl)phenol

Product 1

HCID 27787664-Amino-2,3-difluorophenolYield 74.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

61 g (0.26 mol) of 2,3-difluoro-4-(phenyldiazenyl)phenol from Example 3 and 1 g of Pd/C (10%) are initially charged in 800 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 was concentrated on a rotary evaporator, in the course of which the product already crystallized out. The resulting solid was filtered off, washed with a little cold ethanol and dried under high vacuum for 4 hours. 28 g (74%) of the desired compound were obtained as a light brown powder.

Workup

  1. customThe solution was degassed
  2. filtrationOn completion of hydrogen uptake, the catalyst was filtered off
  3. concentrationthe filtrate was concentrated on a rotary evaporator, in the course of which the product
  4. customalready crystallized out
  5. filtrationThe resulting solid was filtered off
  6. washwashed with a little cold ethanol
  7. customdried under high vacuum for 4 hours

Sources & evidence

ORD record
ord-e098fa1cc7d249be8f61aaffb36a4688
Source dataset
uspto-grants-2008_04
Patent number
US07358397B2

Reaction notes

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