Thionyl Chloride → 2-Chloro-5-(chloromethyl)pyridine

HRID 483347Notes

Reaction equation

HRID 483347 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][N:7]=1>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:3])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 1554792-Chloro-5-(chloromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Thionyl chloride (14.6 ml, 0.2 mol) was added extremely carefully in dropwise manner to a rapidly stirred mixture of 2-chloro-5-hydroxymethylpyridine (18.6 g, 0.13 mol) and chloroform (150 ml) at ambient temperature (20° C.). After addition was complete the resulting mixture was heated under reflux for 12 hours. The reaction mixture was then allowed to cool to ambient temperature (20° C.) and chloroform was evaporated off under reduced pressure to give a brown oil. The product, 2-chloro-5-chloromethyl-pyridine was isolated from this brown oil by flash chromatography using silica gel, 230 to 400 US mesh (0.062 mm to 0.037 mm), with dichloromethane as eluent, as a yellow oil which solidified on standing (17.45 g, 82.9%).

Workup

  1. additionAfter addition
  2. temperaturewas heated
  3. temperatureunder reflux for 12 hours
  4. customwas evaporated off under reduced pressure
  5. customto give a brown oil

Sources & evidence

ORD record
ord-1ed9f7aef82b47c2b7348d3ffad8ff96
Source dataset
uspto-grants-1993_07
Patent number
US05225423

Reaction notes

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