Hydrochloric Acid → 2-Bromo-5-methoxyaniline

HRID 1259058Notes

Reaction equation

HRID 1259058 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.Cl>C(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 2

HCID 313Hydrochloric AcidHCID 792884-Bromo-3-nitroanisole

Product 1

HCID 7930162-Bromo-5-methoxyaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-bromo-4-methoxy-2-nitrobenzene (1.0 eq.), iron powder (3.0 eq.), and concentrated HCl (1.04 eq.) were mixed together in ethanol (0.64 M) and heated to reflux. The reaction was stirred for 24 hours, and the solvent was evaporated. The resulting residue was diluted with ethyl acetate and saturated aqueous ammonium chloride solution. The aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed with water, brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% ethyl acetate in hexane to give the product as oil.

Workup

  1. temperatureheated to reflux
  2. customthe solvent was evaporated
  3. additionThe resulting residue was diluted with ethyl acetate and saturated aqueous ammonium chloride solution
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated en vacuo
  8. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-f786a5bd6c6d4a538bc9d7da0fe7d8d8
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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