Water → 3-Bromo-2-methoxy-4,6-dimethylpyridine

HRID 1043896Notes

Reaction equation

HRID 1043896 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8].[CH3:11][O-:12].[Na+].O>CN(C=O)C>[Br:1][C:2]1[C:3]([O:12][CH3:11])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 866863303-Bromo-2-chloro-4,6-dimethylpyridine

Product 1

HCID 866863313-Bromo-2-methoxy-4,6-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-2-chloro-4,6-dimethylpyridine (2.97 g) and sodium methoxide (11.0 mL, 28% solution in methanol) was stirred in a DMF solvent (30 mL) at 80° C. for 36 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%) to give the title compound (2.33 g).

Workup

  1. extractionfollowed by extraction with diethyl ether
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 10%)

Sources & evidence

ORD record
ord-a95e578701a543c89eb38112802a19ff
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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