Bromine → 4-Bromo-2-methoxy-6-methylaniline

HRID 880697Notes

Reaction equation

HRID 880697 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:4]=1[NH2:5].[Br:11]Br>CO.C(O)(=O)C>[Br:11][C:8]1[CH:7]=[C:6]([CH3:10])[C:4]([NH2:5])=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 4592492-Methoxy-6-methylaniline

Product 1

HCID 106802184-Bromo-2-methoxy-6-methylanilineYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To an ice-water cooled solution of 2-methoxy-6-methylaniline (10 g, 72.9 mmol) in 30 mL of methanol and 10 mL of acetic acid was added dropwise bromine (3.75 mL, 72.9 mmol). The reaction mixture was allowed to stand for overnight. The solvent was removed under reduced pressure and the residue was suspended in 60 mL of IN NaOH and extracted with ethyl acetate and dried over sodium sulfate and evaporated to dryness to give reddish crude product, which was recrystallized from hexane to give pure product (14.3 g, 91%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customto give reddish crude product, which
  6. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-cd8e93922f9c4ca6baf4f67d55a11f42
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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