Ethanol → 2-(2,2-Difluoroethoxy)benzenamine

HRID 593366Notes

Reaction equation

HRID 593366 reaction equation
[F:1][CH:2]([F:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O.C(O)C.[H][H]>[Pd].C(OCC)(=O)C>[F:1][CH:2]([F:14])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH2:11]

Participants

6

Reactant 3

HCID 702EthanolHCID 19622878HCID 19622878, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 196278712-(2,2-Difluoroethoxy)benzenamineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The 1-(2,2-difluoro-ethoxy)-2-nitro-benzene (2.16 mmol) was dissolved in a 1:1-mixture of ethanol and ethyl acetate in order to obtain a final concentration of 0.05M. Hydrogenation was performed at 60° C., 1 bar of hydrogen and with palladium on charcoal (10%) as the catalyst. After evaporation of the solvent the title compound was obtained in 90% yield and could be used in the next step without further purification; (calculated) C8H9F2NO [173.16]; (found) [M+H]+=174.

Workup

  1. customwas performed at 60° C.
  2. customAfter evaporation of the solvent the title compound
  3. customwas obtained in 90% yield
  4. customcould be used in the next step without further purification

Sources & evidence

ORD record
ord-ba5629b7e3164c258cbdeb90b263c03f
Source dataset
uspto-grants-2016_01
Patent number
US09242943B2

Reaction notes

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