4-(Bromomethyl)tetrahydropyran is an important organic synthesis intermediate, widely used in the fields of medicine, pesticides and dyes. It can be used to synthesize a variety of biologically active compounds, such as antibacterial agents, anti-tumor drugs, nervous system drugs and fluorescent dyes. In addition, 4-(Bromomethyl)tetrahydropyran can also be used to synthesize organic pigments and functional materials.
To a solution of Tetrahydropyran-4-methanol and N-bromobutanimide (NBS) in DCM was added PPh3 at 0°C. The reaction mixture was stirred at room temperature for 1–2h. The resulting mixture was washed with water (20mL) and brine (3×20mL). The organic layer was concentrated and the residue was purified by silica gel flash chromatography (eluting with ethyl acetate in petroleum ether 2–5%) to give 4-(Bromomethyl)tetrahydropyran as a colorless oil.
