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

HRID 1420826Notes

Reaction equation

HRID 1420826 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>O.C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[NH2:10]

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 3-bromo-4-methoxynitrobenzene (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 heated under reflux for 2 h. The mixture was cooled and filtered through a pad of Hyflo™, washing with 25% acetic acid/water. The filtrate was extracted with ethyl acetate (2×250 ml) and the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/EtOAc (60:40) to give the title compound as a brown solid (10.32 g, 79%). m/z (ES+) 202 (M+1).

Workup

  1. temperatureunder reflux for 2 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through a pad of Hyflo™
  4. washwashing with 25% acetic acid/water
  5. extractionThe filtrate was extracted with ethyl acetate (2×250 ml)
  6. dry with materialthe combined organic fractions were dried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica eluting with hexane/EtOAc (60:40)

Sources & evidence

ORD record
ord-3d09e2da9e204176b3c8a0cbefc88233
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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