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

HRID 1420680Notes

Reaction equation

HRID 1420680 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH3:12]>O.C(O)(=O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([O:11][CH3:12])=[C:2]([Br:1])[CH:7]=1

Participants

5

Reactant 1

HCID 788702-Bromo-4-nitroanisole

Product 1

HCID 9610833-Bromo-4-methoxyanilineYield 79.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture 2-bromo-4-nitroanisole (15 g, 64.6 mmol) and iron powder (27.3 g, 0.49 mol) in water (100 ml) and glacial acetic acid (25 ml) was stirred at reflux for 2 hours. The mixture was allowed to cool to ambient temperature and filtered through a pad of Hyflo™ (washed with 25% acetic acid/water). The filtrate was extracted with ethyl acetate (2×250 ml) and the organic layer was dried over sodium sulphate. Removal of the solvent in vacuo left an oil which was chromatographed on silica eluting with 40% ethyl acetate/hexane to give the title compound as a brown solid (10.32 g, 79%); m/z (ES+) 202 ([M+H]+).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered through a pad of Hyflo™ (washed with 25% acetic acid/water)
  3. extractionThe filtrate was extracted with ethyl acetate (2×250 ml)
  4. dry with materialthe organic layer was dried over sodium sulphate
  5. customRemoval of the solvent in vacuo
  6. waitleft an oil which
  7. customwas chromatographed on silica eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a07b72d3a91142e492252a2dfc1e9d03
Source dataset
uspto-grants-2000_06
Patent number
US06071928

Reaction notes

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