Chloroform → 3-Bromo-6-methoxy-2-methylpyridine

HRID 1921323Notes

Reaction equation

HRID 1921323 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].IC.[CH:12](Cl)(Cl)Cl>C(=O)([O-])[O-].[Ag+2].C(N(CC)CC)C>[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([O:9][CH3:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 6328Methyl iodideHCID 27344173-Bromo-6-hydroxy-2-methylpyridine

Product 1

HCID 107981463-Bromo-6-methoxy-2-methylpyridineYield 63%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5-bromo-6-methyl-1H-pyridin-2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2-methylpyridine (3.7 g, 63% yield) as an oil. LC/MS RT 3.76 min; MS m/e=202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (1H, d), 3.89 (3H, s), 2.57 (3H, s).

Workup

  1. stirringstirring
  2. waitcontinued for 1.5 hr
  3. filtrationThe reaction mixture is filtered through a pad of Hi-Flo
  4. washthe filtrate is washed with water (100 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate
  9. concentrationThe solvent is concentrated

Sources & evidence

ORD record
ord-9710f8b4226d407eb8f59d8ce57d0962
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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