2-Chloro-4-iodopyridine → 2-Ethoxy-4-iodopyridine

HRID 922564Notes

Reaction equation

HRID 922564 reaction equation
Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[O-:9][CH2:10][CH3:11].[Na+]>CCO>[CH2:10]([O:9][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1)[CH3:11]

Participants

4

Reactant 2

HCID 15165112-Chloro-4-iodopyridineHCID 2723922Sodium ethoxide

Product 1

HCID 666107722-Ethoxy-4-iodopyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 40.0 g (167 mmol) of 2-chloro-4-iodopyridine and 70.0 ml (188 mmol) of sodium ethoxide in 80 ml EtOH is stirred at reflux over night. The solvent is removed in vacuo. The residue is extracted with water and DCM. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. The residue is purified by flash chromatography (silica gel, DCM).

Workup

  1. temperatureat reflux over night
  2. customThe solvent is removed in vacuo
  3. extractionThe residue is extracted with water and DCM
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo
  7. customThe residue is purified by flash chromatography (silica gel, DCM)

Sources & evidence

ORD record
ord-f7f6617ec04143ceaa7c37291023b2cf
Source dataset
uspto-grants-2016_03
Patent number
US09278954B2

Reaction notes

Loading…