Thionyl Chloride → 2-Chloro-4-(chloromethyl)-6-methylpyridine

HRID 2113634Notes

Reaction equation

HRID 2113634 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[C:4]([CH3:10])[N:3]=1.S(Cl)([Cl:13])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][Cl:13])[CH:5]=[C:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22504306(2-Chloro-6-methylpyridin-4-yl)methanol

Product 1

HCID 216981672-Chloro-4-(chloromethyl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.2 1.14 g of (2-chloro-6-methylpyridin-4-yl)methanol are initially introduced in 50 ml of toluene, and 1.05 ml of thionyl chloride are slowly added dropwise with ice cooling. The mixture is boiled under reflux overnight. After cooling, the solvent is removed, giving 2-chloro-4-chloromethyl-6-methylpyridine as brown oil (1.1 g).

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. customthe solvent is removed

Sources & evidence

ORD record
ord-e624334278f045eebad3125f2b59d0fb
Source dataset
uspto-grants-2008_10
Patent number
US07432282B2

Reaction notes

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