1-(Difluoromethoxy)-2-nitrobenzene → 2-(Difluoromethoxy)aniline

HRID 2294106Notes

Reaction equation

HRID 2294106 reaction equation
[F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-])=O>[Pd].C(O)C>[F:1][CH:2]([F:13])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10]

Participants

4

Reactant 1

HCID 27370111-(Difluoromethoxy)-2-nitrobenzene

Product 1

HCID 9346202-(Difluoromethoxy)anilineYield 74,424%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-difluoromethoxy-2-nitrobenzene (8.21 g, 43.4 mmol) and 10% palladium on carbon (1.1 g) in 100 mL of ethanol was stirred under a hydrogen atmosphere at room temperature for approximately 24 hours. The mixture was filtered and the filtrate was concentrated to give 2-difluoromethoxyaniline (5.14 g, 32.3 mol) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-13e38dca0baf48c986d1c223c3f2e5fe
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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