Methyl iodide → 3-Bromo-6-methoxy-2,4-dimethylpyridine

HRID 1043891Notes

Reaction equation

HRID 1043891 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([OH:9])=[N:6][C:7]=1[CH3:8].[CH3:11]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH3:11])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178429301HCID 178429301, compound

Product 1

HCID 112413813-Bromo-6-methoxy-2,4-dimethylpyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 5-bromo-4,6-dimethylpyridin-2-ol (7 g), methyl iodide (21.6 mL) and silver carbonate (19.1 g) was stirred in a chloroform solvent (140 mL) at room temperature for 36 hours. The reaction mixture was subjected to silica gel pad and eluted with a mixed solvent of (ethyl acetate:n-heptane=2:8). The resulting solution was concentrated under reduced pressure to give the title compound (6.98 g).

Workup

  1. washeluted with a mixed solvent of (ethyl acetate:n-heptane=2:8)
  2. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2bbf8354a93e46638d1774e6b237c70c
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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