Water → 2,6-Dibromo-3-methoxypyridine

HRID 2391743

Reaction equation

HRID 2391743 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.[C:10]([O-])([O-])=O.[K+].[K+].CI.O>CS(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 810772,6-Dibromopyridin-3-ol

Product 1

HCID 113346372,6-Dibromo-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 52.5 g 2,6-dibromopyridin-3-ol (example E1) in 90 ml DMSO were added 26.2 g K2CO3 and 43.8 ml methyl iodide and the reaction mixture was stirred under reflux for one hour. The mixture was allowed to cool down to room temperature and poured into 1 l of water and stirred for 3 h at 80° C. After cooling to room temperature the resulting solid was filtered, the filter cake was washed with ice cold water and dried under vacuum to yield the title compound.

Workup

  1. temperatureunder reflux for one hour
  2. stirringstirred for 3 h at 80° C
  3. temperatureAfter cooling to room temperature the resulting solid
  4. filtrationwas filtered
  5. washthe filter cake was washed with ice cold water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-e5beefebb0a44d4eaeed350d335a5d50
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Linked notes

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