Methyl iodide → 2-Bromo-3-methoxy-6-methylpyridine

HRID 488814Notes

Reaction equation

HRID 488814 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 119591012-Bromo-6-methylpyridin-3-ol

Product 1

HCID 109655632-Bromo-3-methoxy-6-methylpyridineYield 88.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 2-bromo-3-hydroxy-6-methyl-pyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol) and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) in acetone (100 mL) was heated under reflux overnight. The mixture was filtered, evaporated and purified on silica gel (hexane:ethyl acetate, 95:5 to 9:1) to give the desired product as a white solid (7.49 g, 88.3%). 1H NMR (500 MHz, CDCl3): δ 2.46 (s, 3 H), 3.87 (s, 3 H), 7.04 (s, 2 H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. custompurified on silica gel (hexane:ethyl acetate, 95:5 to 9:1)

Sources & evidence

ORD record
ord-58635002450b4ed6aaeee81ac6a86c27
Source dataset
uspto-grants-2005_12
Patent number
US06974826B2

Reaction notes

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