3-Fluoro-4-nitroanisole → 2-Fluoro-4-methoxyaniline

HRID 638989Notes

Reaction equation

HRID 638989 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[C:5]([F:12])[CH:4]=1>C(O)C.[Pd]>[F:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH2:9]

Participants

4

Reactant 1

HCID 5656543-Fluoro-4-nitroanisole

Product 1

HCID 37563832-Fluoro-4-methoxyanilineYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-fluoro-4-nitrophenyl methyl ether (28.1 g, 164 mmol) in ethanol (200 mL) was hydrogenated with palladium on charcoal. The reaction mixture was filtered through Kieselguhr and evaporated under vacuum to afford the product as an oil (22.8 g, 98%); MS (+ve ion electrospray) m/z 141 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered through Kieselguhr
  2. customevaporated under vacuum

Sources & evidence

ORD record
ord-7c75fe74df6a4fff82dd53bdd71fe028
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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