4-Bromo-3-methoxyaniline → 4-Bromo-3-methoxyphenol

HRID 581985Notes

Reaction equation

HRID 581985 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[Br:10])N.N([O-])=[O:12].[Na+]>O.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:7]=[CH:8][C:9]=1[Br:10]

Participants

5

Reactant 2

HCID 70182544-Bromo-3-methoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 3479554-Bromo-3-methoxyphenolYield 69.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 1118Sulfuric AcidSolvent2×

Procedure

3-Methoxy-4-bromoaniline (D1) (10.0 g, 49 mmoles) in water (60 ml) and concentrated sulphuric acid (30 ml) was treated with a solution of sodium nitrite (3.4 g, 49 mmoles) in water (15 ml) dropwise keeping the temperature below 5° C. The resulting slurry was then added slowly to a mixture of water (60 ml) and concentrated sulphuric acid (30 ml) at 80° C. and stirred at this temperature for 3 hrs. The mixture was cooled and extracted with dichloromethane (2×200 ml). The organics were then extracted with 2N sodium hydroxide solutions (2×100 ml). The aqueous was washed with more dichloromethane (2×200 ml) then acidified to pH 1. Extraction with dichloromethane, drying (Na2SO4) and evaporation to dryness gave the title compound (D8) (6.95 g, 69%).

Workup

  1. customthe temperature below 5° C
  2. temperatureThe mixture was cooled
  3. extractionextracted with dichloromethane (2×200 ml)
  4. extractionThe organics were then extracted with 2N sodium hydroxide solutions (2×100 ml)
  5. washThe aqueous was washed with more dichloromethane (2×200 ml)
  6. extractionExtraction with dichloromethane
  7. customdrying
  8. custom(Na2SO4) and evaporation to dryness

Sources & evidence

ORD record
ord-c0e242a4d47248f893f2c3b722479e90
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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