4-Bromo-3-nitroanisole → 2-Bromo-5-methoxyaniline

HRID 401222Notes

Reaction equation

HRID 401222 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O>C(O)C.[Ni]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 1

HCID 792884-Bromo-3-nitroanisole

Product 1

HCID 7930162-Bromo-5-methoxyanilineYield 86.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-bromo-4-methoxy-2-nitro-benzene (10 g, 43 mmol) and Raney Ni (5 g) in ethanol (100 mL) was stirred under H2 (1 atm) for 4 h at room temperature. Raney Ni was filtered off and the filtrate was concentrated under reduced pressure. The resulting solid was purified by column chromatography to give 2-bromo-5-methoxy-phenylamine (7.5 g, 86%).

Workup

  1. filtrationRaney Ni was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting solid was purified by column chromatography

Sources & evidence

ORD record
ord-f46df8e9af7548f58b650a1f440cdd3f
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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