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

HRID 330811Notes

Reaction equation

HRID 330811 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

To 2.00 g (8.35 mmol) 2-chloro-4-iodopyridine in 15 mL ethanol are added 3.4 mL (9.2 mmol) sodium ethoxide and stirred at reflux for 12 h. The solvent is evaporated in vacuo and the residue is partitioned between water and DCM. The organic layer is dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel; DCM/MeOH gradient 100/0→96/4).

Workup

  1. temperatureat reflux for 12 h
  2. customThe solvent is evaporated in vacuo
  3. customthe residue is partitioned between water and DCM
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silica gel; DCM/MeOH gradient 100/0→96/4)

Sources & evidence

ORD record
ord-8142f9101be64e36b2c5e5f70a56c150
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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