Methyl iodide → 6-Bromo-3-methoxy-2,4-dimethylpyridine

HRID 1662208Notes

Reaction equation

HRID 1662208 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.IC.[C:13](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:13])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593274926-Bromo-2,4-dimethylpyridin-3-ol

Product 1

HCID 593275316-Bromo-3-methoxy-2,4-dimethylpyridineYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-bromo-2,4-dimethyl-3-hydroxypyridine (8.7 g, 43.1 mmol), iodomethane (4.0 mL, 64.6 mmol) and potassium carbonate (11.9 g, 86.1 mmol) in acetone (250 mL) was heated at reflux temperature for 3 hours. The reaction mixture was then cooled to room temperature and filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography using 20% ethyl acetate in hexane to afford 7.9 g (85%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 3 hours
  3. filtrationfiltered through a pad of Celite®
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-76de05dbfe964f4290e4bd267e8486fe
Source dataset
uspto-grants-2011_10
Patent number
US08030500B2

Reaction notes

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