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

HRID 1632013Notes

Reaction equation

HRID 1632013 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+].CI>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 36.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To the 2-bromo-6-methyl-pyridin-3-ol (I-2) 6.0 g, 31.91 mmol) and K2CO3 (8.82 g, 63.82 mmol) in acetone (100 mL) was added MeI (6.79 g, 479.87 mmol). The reaction was stirred at 45° C. under N2 for 20 h. The reaction was cooled to room temperature, filtered and concentrated. The residue was purified by silica gel column chromatography using 1:1 dichloromethane-hexanes as eluent to afford 2.34 g (36%) of 2-bromo-3-methoxy-6-methyl-pyridine (I-3, X═Br, Y═R1═CH3) as off-white solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-11dfd57394af4948b2968b56ecd9742d
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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