Benzyl Bromide → HCID 10195506, compound

Participants

Reaction Steps

To a solution of 2-[4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-phenol (30 mg, 0.0783 mmol) in 3 mL of ethanol were added potassium carbonate (16 mg, 0.117 mmol), benzyl bromide (11 μL, 0.0940 mmol) and tetrabutylammonium iodide (3 mg, 0.1 mmol). The reaction mixture was heated at gentle reflux for 54 h. Additional benzyl bromide (11 μL) and potassium carbonate (16 mg) were added after every 24-hr. Upon cooling to room temperature, the solvent was removed and the residue was taken in methylene chloride. The solution was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 1-6% methanol in methylene chloride yielded 2-(2-benzyloxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazole (16.3 mg, 44%). HR-MS (ES, m/z) calculated for C28H23N2OCl2 [(M+H)+] 473.1185, observed 473.1183.

Provenance & Evidence