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

HRID 1246627Notes

Reaction equation

HRID 1246627 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>O.C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

5

Reactant 1

HCID 792884-Bromo-3-nitroanisole

Product 1

HCID 7930162-Bromo-5-methoxyanilineYield 57.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-Bromo-3-nitroanisole (10 g, 43 mmol) and iron powder (21.72 g, 385 mmol) were stirred in a mixture of water (10 mL) and acetic acid (100 mL) for 1.5 h. The solvent was removed in vacuo, the brown residue was taken up in water (200 mL) and treated with 10% aq K2CO3 until pH 10. The mixture was extracted with EtOAc (4×150 mL) and the combined organic extracts were dried (MgSO4) and evaporated to give the desired aniline (5.0 g, 57%) as a brown oil; δH (CDCl3, 400 MHz) 3.72 (3H, s), 4.05 (2H, br), 6.22 (1H, dd), 6.32 (1H, d), 7.26 (1H, d); MS m/z (TS+) 202, 204 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. additiontreated with 10% aq K2CO3 until pH 10
  3. extractionThe mixture was extracted with EtOAc (4×150 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fd0e8ab391504de79c24d48d9630da2a
Source dataset
uspto-grants-2006_10
Patent number
US07129234B2

Reaction notes

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