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

HRID 76125Notes

Reaction equation

HRID 76125 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+]>C(O)C>[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

2.0 g (8.35 mmol) 2-chloro-4-iodopyridine and 3.4 mL (9.19 mmol) sodium ethoxide are added to 15 mL ethanol and stirred at reflux over night. The solvent is evaporated in vacuo and the residue is partitioned between water and DCM. The organic layer is dried (Na2SO4) and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 100/0→96/4).

Workup

  1. temperatureat reflux over night
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is partitioned between water and DCM
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel, DCM/MeOH 100/0→96/4)

Sources & evidence

ORD record
ord-005186bda66b47a5a767f5ba12eda1d5
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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