Pyridine → 2-Chloro-5-(chloromethyl)pyridine

HRID 1089438Notes

Reaction equation

HRID 1089438 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=1.N1C=CC=CC=1>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Cl:3])=[CH:10][N:11]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridine

Procedure

85 ml of thionyl chloride are added cautiously to 14.4 g (0.1 mol) of 6-chloro-pyridine-3-methanol. 8.1 g (0.1 mol) of pyridine are then added dropwise and the mixture is heated under reflux until gas evolution is complete. Excess thionyl chloride is removed in vacuo and the residue is poured onto ice. The precipitate is filtered off with suction and dried. Yield 10.6 g (65.5% of theory), m.p.: 38°-40° C. The crude product can be used further without purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux until gas evolution
  3. customExcess thionyl chloride is removed in vacuo
  4. additionthe residue is poured onto ice
  5. filtrationThe precipitate is filtered off with suction
  6. customdried
  7. customThe crude product can be used further without purification

Sources & evidence

ORD record
ord-fa57a70488164c509d6c99a82a298245
Source dataset
uspto-grants-1990_10
Patent number
US04966902

Reaction notes

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