Uses
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.
Application
4-(Bromomethyl)tetrahydropyran can be used as an intermediate in the synthesis of compounds with antibacterial activity. For example, it can be used to introduce other functional groups through nucleophilic substitution reactions to construct molecules with antibacterial activity. Certain compounds containing tetrahydropyran rings have been studied for their potential to inhibit bacterial growth and reproduction.
Synthesis
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.
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 896 - 916
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 5512,5514
[3] Justus Liebigs Annalen der Chemie, 1937, vol. 532, p. 80
[4] Chem.Abstr., 1940, p. 4396
[5] Journal of the American Chemical Society, 1993, vol. 115, # 18, p. 8401 - 8408
