2-Methoxyaniline → 3-Bromo-2-methoxyaniline

HRID 1596599Notes

Reaction equation

HRID 1596599 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[Br:10]Br>C(O)(=O)C>[Br:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 70002-MethoxyanilineHCID 24408Bromine

Product 1

HCID 226677353-Bromo-2-methoxyanilineYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a cooled solution of 2-anisidine (2.7 mL, 23.7 mmol) in cetic acid (20 mL) at 10° C. was slowly added a solution of bromine (1.22 mL, 23.7 mmol) in acetic acid (10 mL) over a 10 min period. After stirring for 10 min, the solvents were removed by rotoevaporation and the residue dissolved in ethyl acetate. This solution was successively washed with saturated sodium bicarbonate solution and dried over anhydrous magnesium sulfate. After filtering, the solvents were removed by rotoevaporation and the product purified by flash column chromatography on silica gel eluted with 45% methylene chloride in hexanes to yield 3.44 g (72% yield) of the title compound.

Workup

  1. customthe solvents were removed by rotoevaporation
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washThis solution was successively washed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering
  6. customthe solvents were removed by rotoevaporation
  7. customthe product purified by flash column chromatography on silica gel
  8. washeluted with 45% methylene chloride in hexanes

Sources & evidence

ORD record
ord-698befa3157a4ff5b442a2cdfe9c7740
Source dataset
uspto-grants-2001_09
Patent number
US06291511B1

Reaction notes

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