Phosphorus oxychloride → 2-(4-Methylphenyl)-6-chloromethylpyridine

Participants

Reaction Steps

To a solution of 2-(4-methylphenyl)-6-methylpyridine-N-oxide (2.8 g) in 10 ml of chloroform was added simultaneously phosphorus oxychloride (1.48 ml) in 10 ml of chloroform and triethylamine (2.22 ml) in 10 ml of chloroform, over a period of 15 minutes. An exothermic reaction took place initially, and then the mixture was refluxed for a further 30 minutes. The mixture was then cooled, washed with ice-water, the solvent evaporated under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 33% methylene chloride in heptane, to yield 1 g of 2-(4-methylphenyl)-6-chloromethylpyridine, m.p. 94° C.

Provenance & Evidence