Thionyl Chloride → 2-Chloro-6-(chloromethyl)pyridine

HRID 2050772Notes

Reaction equation

HRID 2050772 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][Cl:12])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 182139(6-Chloropyridin-2-yl)methanolHCID 516892Sodium Bicarbonate

Product 1

HCID 155744402-Chloro-6-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Chloro-2-pyridylmethanol, 0.982 g (6.84 mmole) in 10 ml methylene chloride was treated with 0.814 g thionyl chloride at room temperature for one hour. The mixture was neutralized with saturated sodium bicarbonate solution, extracted with methylene chloride, the extracts dried and solvent evaporated to give 815 mg of product as colorless crystals. 1H-NMR(CDCl3)ppm (delta): 4.7 (s, 2H), 7.1-8.0 (m, 3H).

Workup

  1. extractionextracted with methylene chloride
  2. customthe extracts dried
  3. customsolvent evaporated

Sources & evidence

ORD record
ord-5a5768264e0d43c5aabee74a9a77fd86
Source dataset
uspto-grants-1991_05
Patent number
US05015473

Reaction notes

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