Yield:58539-77-8 87%

Reaction Conditions:

with thionyl chloride in chloroform;toluene at 20 - 35; for 1 h;

Steps:

6

A solution of this alcohol compound (29.9 g, 234 mmol) in 110 ml CHCl₃ was added dropwise to a solution of SOCl₂ (18.6 ml, 256 mmol) in 26 ml toluene, all the while maintaining the internal temperature between 23° and 35°. After the end of the addition the reaction mixture was vigorously stirred at room temperature for 1 h and water pump vacuum was applied until the solvent was completely evaporated. The brown precipitate was resuspended in toluene, rapidly filtered off and washed three times with toluene. Drying in the desiccator (aspirator vacuum) gave 35.9 g (202 mmol, 87%) of 3-(chloromethyl)-2-methylpyridine hydrochloride as a brown solid. GC-analysis of the free base indicated a purity of 100%.

References:

US2005/124586,2005,A1 Location in patent:Page/Page column 10