Benzyl Bromide → HCID 178515913, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, a rubber septum and a reflux condenser was charged with acetone (25 mL), 4-(2H-tetrazol-5-yl)phenol (50 mg, 0.31 mmol) and K2CO3 (213 mg, 1.54 mmol). The reaction mixture was treated with benzylbromide (37 μL, 0.31 mmol) and heated at 50° C. for 18 h. The reaction mixture was cooled to ambient temperature and filtered to remove the K2CO3 and the filtrate was concentrated to dryness. The resulting residue was triturated with 3 M aqueous NaOH and extracted with ethyl acetate. The aqueous phase was separated and treated with HCl (conc.). The precipitate was collected and subjected to flash chromatography (SiO2, 30% ethyl acetate/hexane) to afford the title product as a white solid (57 mg, 74%). This procedure was repeated on a 3 g scale in 50% yield.

Provenance & Evidence