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

HRID 1761399Notes

Reaction equation

HRID 1761399 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.[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 5360545Sodium

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 bicaronate 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-9b1184cb7ddf4a91b1282065fb09db94
Source dataset
uspto-grants-1989_05
Patent number
US04826833

Reaction notes

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