Phosphorus oxychloride → 2,4-Dichloro-5-(chloromethyl)pyridine

HRID 1701176Notes

Reaction equation

HRID 1701176 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([CH2:9]O)=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:13])=O>>[Cl:13][CH2:9][C:5]1[C:6]([Cl:8])=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 2762727(4,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 27627282,4-Dichloro-5-(chloromethyl)pyridine

Procedure

20.2 g. of 2,4-dichloropyridin-5-methanol (0.11 mol.) and 150 ml. of phosphorus oxychloride are refluxed for 19 hours. Then the excess phosphorus oxychloride is removed in vacuo and ice is added to the residue. 5-Chloromethyl-2,4-dichloropyridine is filtered off, washed with water, dried in the desiccator over P2O5 and recrystallized from hexane; yield 17.95 g. (83%), m.p. 55°-56°.

Workup

  1. customThen the excess phosphorus oxychloride is removed in vacuo and ice
  2. additionis added to the residue
  3. filtration5-Chloromethyl-2,4-dichloropyridine is filtered off
  4. washwashed with water
  5. dry with materialdried in the desiccator over P2O5
  6. customrecrystallized from hexane

Sources & evidence

ORD record
ord-285f929e1d7740bcb9c1e9b9361a3547
Source dataset
uspto-grants-1980_03
Patent number
US04191831

Reaction notes

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