Acetic Acid → 5-Bromo-3-methoxy-2-methylaniline

HRID 629509Notes

Reaction equation

HRID 629509 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[C:4]([O:12][CH3:13])[CH:3]=1.C(O)(=O)C>[Fe].C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH3:13])[C:5]([CH3:11])=[C:6]([CH:7]=1)[NH2:8]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 247281025-Bromo-1-methoxy-2-methyl-3-nitrobenzene

Product 1

HCID 272747255-Bromo-3-methoxy-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A heterogeneous reaction mixture of 4-bromo-2-methoxy-6-nitrotoluene (500 mg, 2.032 mmol), acetic acid (20 ml), and iron (1135 mg, 20.32 mmol) was stirred at rt for 24 hr. Ethyl acetate was added, then the mixture was filtered through celite and the filtrate concentrated. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with further ethyl acetate. The combined organic phases were washed with water and brine, then dried over sodium sulfate, filtered and concentrated to afford the title compound. MS m/z: 218.0 (M+H)+.

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationthe filtrate concentrated
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionThe aqueous layer was extracted with further ethyl acetate
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8859f3d5a022483f975f49a9bec80ff7
Source dataset
uspto-grants-2016_04
Patent number
US09314464B2

Reaction notes

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