Thionyl Chloride → 3-Chloro-4-(chloromethyl)pyridine

HRID 2401703Notes

Reaction equation

HRID 2401703 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]O.S(Cl)([Cl:12])=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][Cl:12]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 12742466(3-Chloropyridin-4-yl)methanol

Product 1

HCID 148510673-Chloro-4-(chloromethyl)pyridineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 0.70 g of (3-chloropyridin-4-yl)methanol and 8 ml of chloroform was added dropwise 0.70 g of thionyl chloride at room temperature, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, and the mixture was extracted twice with chloroform. The organic layers were combined and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 0.78 g of 3-chloro-4-(chloromethyl)pyridine.

Workup

  1. extractionthe mixture was extracted twice with chloroform
  2. dry with materialdried over magnesium sulfate
  3. concentrationThe resulting mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9dc7a2bcc80e4bb1b5e206ae246eea3f
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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