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

HRID 1975746Notes

Reaction equation

HRID 1975746 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[N:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:5][C:6]1[N:11]=[C:10]([CH2:12][Cl:3])[CH:9]=[CH:8][CH:7]=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 6212ChloroformSolvent2×

Procedure

Thionyl chloride (12.6 mL; 173 mmol) in 100 mL chloroform was added dropwise to a solution of 6-chloro-2-hydroxymethylpyridine (13.0 g; 90.5 mmol), prepared as in step 3, in 100 mL chloroform. Upon complete addition the reaction mixture was heated at reflux for 2 hours. The reaction mixture was cooled to ambient temperature and carefully poured into 250 mL saturated aqueous sodium bicarbonate. The layers were separated and the aqueous was extracted with dichloromethane. The extracts were dried over magnesium sulfate and concentrated. 6-chloro-2-chloromethylpyridine was isolated as a pale yellow solid by flash chromatography (20% diethyl ether in hexane).

Workup

  1. additionUpon complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with dichloromethane
  6. dry with materialThe extracts were dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-70605b592c9d4c4ca18f4fe14c80cc1c
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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