Methyl iodide → 3-Bromo-2-methoxy-5-methylpyridine

HRID 554648Notes

Reaction equation

HRID 554648 reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.I[CH3:11]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:3]([O:9][CH3:11])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178430683HCID 178430683, compound

Product 1

HCID 219527573-Bromo-2-methoxy-5-methylpyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

3-Bromo-2-hydroxy-5-methylpyridine (5.012 g, 26.7 mmol), silver carbonate (9.58 g, 34.7 mmol), and iodomethane (5 mL, 80.0 mmol) were combined in CHCl3 (75 mL) and stirred at 55° C. for 3 hours. The mixture was cooled and filtered through Celite, and the filtrate was concentrated and purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 3-bromo-2-methoxy-5-methyl-pyridine.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3b4f135f3db4445382f3496dd8597d2c
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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