Methyl iodide → 2-Bromo-3-methoxypyridine

HRID 1976043Notes

Reaction equation

HRID 1976043 reaction equation
[Br:1][C:2]1(O)[CH:7]=[CH:6][CH:5]=[CH:4][NH:3]1.[C:9](=O)([O-])[O-:10].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:7]([O:10][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22000233HCID 22000233, compound

Product 1

HCID 903642-Bromo-3-methoxypyridineYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

2-Bromo-2-pyridinol (15 g, 86 mmol) in acetone (500 ml) was treated with potassium carbonate (23.8 g, 172 mmol) and iodomethane (8.1 ml, 130 mmol) and the suspension was refluxed at 70° C. for 16 hours. Once cooled, the mixture was filtered and the filtrate concentrated in vacuo. The residue was then purified by silica wet flash chromatography to give the product as yellow crystals (12.4 g, 66 mmol, 77% yield).

Workup

  1. temperatureOnce cooled
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was then purified by silica wet flash chromatography

Sources & evidence

ORD record
ord-e65dfe80ed7040a18e524ce597055171
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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