Water → 2,6-dichloro-4-(chloromethyl)pyridine

HRID 651430Notes

Reaction equation

HRID 651430 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([Cl:10])[N:3]=1.N1C=CC=CC=1.S(Cl)([Cl:19])=O.O>C1(C)C=CC=CC=1.C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:19])[CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 27946262,6-dichloro-4-(chloromethyl)pyridine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

5.0 g of 2,6-dichloro-4-pyridinemethanol and 2.5 ml of pyridine were suspended in 10 ml of toluene, and the suspension was cooled in a salt-ice bath. To this, 2.7 ml of thionyl chloride were added dropwise for 1 hour, and subsequently the reacted solution was stirred at 110° C. for 3 hours. After cooling, water was added to the solution, and extraction was conducted using diethyl ether. The organic phase was washed with water, and was dried by adding sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to obtain 5.0 g of 2,6-dichloro-4-chloromethylpyridine.

Workup

  1. temperaturethe suspension was cooled in a salt-ice bath
  2. temperatureAfter cooling
  3. washThe organic phase was washed with water
  4. customwas dried
  5. additionby adding sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c45572ba7e041ae867c31cb16f18797
Source dataset
uspto-grants-2001_08
Patent number
US06281231B1

Reaction notes

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