2-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene → 3-Fluoro-4-(2-methoxyethoxy)aniline

HRID 1842872Notes

Reaction equation

HRID 1842872 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15]>C(O)C.[H][H].[Pd]>[F:1][C:2]1[CH:7]=[C:6]([CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][O:14][CH3:15])[NH2:8]

Participants

5

Reactant 1

HCID 234980752-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

Product 1

HCID 234981173-Fluoro-4-(2-methoxyethoxy)anilineYield 93.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a stirred solution of 2-fluoro-1-(2-methoxyethoxy)-4-nitrobenzene (2.5 g, 11.62 mmol, 1.0 eq.) in ethanol (20 mL) was added 10% Pd/C (500 mg) and stirred in hydrogen gas atmosphere for 16 h at RT. The catalyst was filtered over a celite pad and the filtrate was concentrated to get 3-fluoro-4-(2-methoxyethoxy)aniline (2.0 g, 93.9%; TLC system: EtOAc/PE (3:7), Rf: 0.3).

Workup

  1. filtrationThe catalyst was filtered over a celite pad
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d02065bbbe7c40c7b9b4e404f671572b
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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