2,3,5-Tribromopyridine → 3,5-Dibromo-2-methoxypyridine

HRID 547675Notes

Reaction equation

HRID 547675 reaction equation
[CH3:1][O-:2].[Na+].Br[C:5]1[C:10]([Br:11])=[CH:9][C:8]([Br:12])=[CH:7][N:6]=1>O>[Br:11][C:10]1[C:5]([O:2][CH3:1])=[N:6][CH:7]=[C:8]([Br:12])[CH:9]=1

Participants

4

Reactant 2

HCID 6287982,3,5-TribromopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 135677523,5-Dibromo-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

80 ml of a 28% sodium methoxide solution was incorporated with 30.0 g of 2,3,5-tribromopyridine under ice-cooling, followed by stirring at 50° C. for 2 hours. The reaction solution was diluted with water and extracted with diethyl ether. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane=1:20), to give 18.5 g of the title compound.

Workup

  1. temperaturecooling
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane=1:20)

Sources & evidence

ORD record
ord-07e98ccb9d514230b2434e95ed4bd1e4
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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