2,6-Dibromopyridine → 2-Bromo-6-ethoxypyridine

HRID 1636185Notes

Reaction equation

HRID 1636185 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].Br[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1>C1(C)C=CC=CC=1.O>[Br:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:1][CH2:2][CH3:3])[N:7]=1

Participants

5

Reactant 2

HCID 122742,6-DibromopyridineHCID 2723922Sodium ethoxide

Product 1

HCID 12010182-Bromo-6-ethoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium ethoxide (1.5 g, 63 mmol sodium, in ethanol (30 ml)) was added to 2,6-dibromopyridine (15 g, 63 mmol) in toluene (150 ml) at ambient temperature under nitrogen, and the reaction heated under reflux for 5 hours. The cooled mixture was diluted with water (100 ml), and extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by column chromatography on silica gel using pentane/ethyl acetate (100:0 to 95:5) as eluant to give the title compound as a yellow oil, (quantitative).

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux for 5 hours
  3. extractionextracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b91aec63491f4d8699e97413d2b70208
Source dataset
uspto-grants-2003_01
Patent number
US06511993B1

Reaction notes

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