2-Bromomethylnaphthalene → HCID 14280704, compound

Participants

Reaction Steps

A mixture of 15.1 g (0.062 mol) 4-(4-fluorobenzoyl)piperidine hydrochloride, 13.77 g (0.062 mol) of 2-(bromomethyl)naphthalene and 13.6 g (0.16 mol) of sodium bicarbonate in 500 mL of absolute ethanol was stirred at room temperature for 16 hr. The solvent was partitioned between CH2Cl2 and dilute NaOH. The CH2Cl2 solution was dried (Na2SO4), and the solvent was removed in vacuo. The residue was recrystallized from 400 mL of methanol to give 11.81 g (54.9%) of white crystalline solid, mp 131°-134° C. The filtrate was subjected to flash chromatography (silica gel, gradiently eluted with CH3OH/CH2Cl2) to give an additional 2.84 g (13.2%) of the title compound.

Provenance & Evidence