Methanol → 3-Bromo-5-methoxy-4-methylpyridine

HRID 1521554Notes

Reaction equation

HRID 1521554 reaction equation
[CH3:1][O-:2].[Na+].[Na].CO.[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12](Br)[C:13]=1[CH3:14]>CN(C)C=O.C(OCC)(=O)C>[Br:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:2][CH3:1])[C:13]=1[CH3:14]

Participants

7

Reactant 4

HCID 887MethanolHCID 8193383,5-Dibromo-4-methylpyridineHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 573637893-Bromo-5-methoxy-4-methylpyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a freshly prepared sodium methoxide from sodium metal (0.165 g, 0.0072 mol) and methanol (2.5 mL), 3,5-dibromo-4-methyl-pyridine (1.0 g, 0.0040 mol) dissolved in N,N-dimethylformamide (10 mL) was added and heated at 80° C. overnight. Reaction was diluted with ethyl acetate and quenched with ice water, and layers were separated. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated to provide the title compound. 1H NMR (400 MHz, CDCl3) δ 8.33 (s, 1H), 8.09 (s, 1H), 3.05 (s, 3H), 2.32 (s, 3H).

Workup

  1. additionwas added
  2. customReaction
  3. customquenched with ice water, and layers
  4. customwere separated
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  6. washThe combined organic extracts were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b103602b669d476cb888614d218a9919
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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