2,4-Difluoro-1-(4-nitrophenoxy)benzene → 4-(2,4-Difluorophenoxy)aniline

HRID 392398Notes

Reaction equation

HRID 392398 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1>CO.[Pd]>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 30154092,4-Difluoro-1-(4-nitrophenoxy)benzene

Product 1

HCID 226635574-(2,4-Difluorophenoxy)anilineYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-(2,4-difluorophenoxy)-4-nitrobenzene (209 g, 1.17 mol) and 10% palladium-on-carbon (20 g, 50% wet) in methanol (1.0 L) was shaken under an atmosphere of hydrogen (60 psi) at room temperature for 5 h. The mixture was filtered through a plug of Celite® (150 g), washing with methanol (2×300 mL) and the solvent was removed under reduced pressure to afford the crude product as a dark red oil. This residue was triturated with hexanes (500 mL) and filtered to provide the title compound as a gray solid (175 g, 95%).1H NMR(300 MHz, DMSO-d6): 6.55(2H,d,J=8.8), 6.73(2H,d,J=8.8), 7.02-6.95(2H,m), 7.40(1H,t,J=11.4).

Workup

  1. filtrationThe mixture was filtered through a plug of Celite® (150 g)
  2. washwashing with methanol (2×300 mL)
  3. customthe solvent was removed under reduced pressure
  4. customto afford the crude product as a dark red oil
  5. customThis residue was triturated with hexanes (500 mL)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9418fa36c5fd42df92f756a283425e5a
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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