Hydrochloric Acid → 2-Chloro-5-(chloromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a three necked, 100-mL round bottom equipped with a reflux condenser, gas inlet tube and a thermometer was charged 50 mL of N,N-dimethylformamide. Phosphorous pentachloride (2.3 g, 11 mmol) was added in several portions and anhydrous hydrogen chloride was introduced slowly. The reaction temperature was kept around 60° C.-85° C. by means of a water bath. 2-Chloro-2-chloromethyl-4-cyanobutyraldehyde in 5 mL of DMF was added at 80° C., through a syringe pump within a period of 1 h. The resulting mixture was then heated to 100° C. under stirring for 8 h, quenched with water, neutralized using NaHCO3 to a pH of 5, extracted with methylene chloride, dried over MgSO4, and concentrated and distilled to give 0.5 g of 2-chloro-5-chloromethylpyridine. Purity by GLC analysis was 95%.

Provenance & Evidence