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

HRID 365339Notes

Reaction equation

HRID 365339 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-methoxyaniline

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, 0.49M) in water (100 ml) and glacial acetic acid (25 ml) was stirred at reflux for 2h. 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 in 40% ethyl acetate/hexane giving the title compound as a brown solid (10.32 g, 79%). MS (ES+) 202 (M+1).

Workup

  1. temperatureat reflux for 2h
  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 in 40% ethyl acetate/hexane giving the title compound as a brown solid (10.32 g, 79%)

Sources & evidence

ORD record
ord-8b5fb2683b394cb289604d3c0baf9620
Source dataset
uspto-grants-2000_10
Patent number
US06127365

Reaction notes

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