Sodium hydride → HCID 11183726, compound

Participants

Reaction Steps

p-Fluorobenzyl cyanide (4.1 g), 2-bromo-4-methylpyridine (5.2 g) and sodium p-toluene sulfinate (5.4 g) were suspended in THF (50 ml), and to the solution was added a suspension of 40% sodium hydride (1.2 g) in THF (5 ml) under ice-cooling. The mixture was refluxed for 3 hours, the solvent was distilled off, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give 2-(α-cyano-4-fluorobenzyl)-4-methylpyridine (3.1 g) as brown oil.

Provenance & Evidence