Water → 3-Bromo-5-methoxypyridine

HRID 563883Notes

Reaction equation

HRID 563883 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[CH3:9][O-:10].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:10][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 693693,5-DibromopyridineHCID 10942334Sodium Methoxide

Product 1

HCID 8171633-Bromo-5-methoxypyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,5-Dibromopyridine (30.0 g) was added to a stirred solution of sodium methoxide (prepared from 11.6 g of sodium) in methanol (120 ml) and heated to reflux for 70 hours under an atmosphere of nitrogen. The mixture was cooled to ambient temperature, poured into water (1000 ml), extracted with diethyl ether and the extracts combined, washed with water and dried over magnesium sulphate. The solvent was evaporated to give 3-bromo-5-methoxypyridine as a colourless liquid, which slowly crystallised on storing (19.3 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 70 hours under an atmosphere of nitrogen
  3. extractionextracted with diethyl ether
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-4e188d157d92433aa5d03577bff2d186
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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