Methanol → 5-Bromo-2-methoxypyridine

HRID 353217Notes

Reaction equation

HRID 353217 reaction equation
[Na].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][N:4]=1.[CH3:10][OH:11]>>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([O:11][CH3:10])=[N:4][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 693532,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 83%

Procedure

After sodium (10 g, 0.435 mol) was dissolved in methanol (500 ml), 2,5-dibromopyridine (50 g, 0.211 mol) was added thereto and the mixture was heated for 2 days under reflux. The reaction solution was cooled as it was, and then concentrated. Then, the residue was diluted with ethyl acetate and an aqueous saturated solution of ammonium chloride. The organic layer was washed with an aqueous saturated solution of ammonium chloride and brine, and then dried over anhydrous sodium sulfate and concentrated, to give the title compound (33 g, 83%) as a pale brown oil.

Workup

  1. temperaturethe mixture was heated for 2 days
  2. temperatureunder reflux
  3. temperatureThe reaction solution was cooled as it
  4. concentrationconcentrated
  5. additionThen, the residue was diluted with ethyl acetate
  6. washThe organic layer was washed with an aqueous saturated solution of ammonium chloride and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-1e055365b5fb462696d8640898dde366
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

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