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

HRID 2407762Notes

Reaction equation

HRID 2407762 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[O-:9][CH2:10][CH3:11].[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:9][CH2:10][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 122742,6-DibromopyridineHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxide

Product 1

HCID 12010182-Bromo-6-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,6-dibromopyridine (1.5 g) in ethanol (6 mL) was treated with sodium ethoxide (3.55 mL) solution dropwise and resulting mixture was refluxed for 18 hours. The mixture was allowed to cool to room temperature and poured into a beaker containing 5% sodium bicarbonate, extracted with diethyl ether. The combined organics were washed with brine, dried, evaporated in vacuo and purified by column chromatography on silica gel (1-3% methanol in dichloromethane) to obtain the title compound (0.840 g) having the following physical data.

Workup

  1. customresulting mixture
  2. temperaturewas refluxed for 18 hours
  3. additionpoured into a beaker
  4. extractionextracted with diethyl ether
  5. washThe combined organics were washed with brine
  6. customdried
  7. customevaporated in vacuo
  8. custompurified by column chromatography on silica gel (1-3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-dda19bd54e864dd7af8f8636365ab956
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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