Uses
1-(Bromomethyl)-3-phenoxybenzene-d5 is an intermediate in the synthesis of Etofenprox-phenol-d5 (E936401) which is a labelled form of Etofenprox (E936400), which is a pyrethroid derivative which is used as an insecticide. Used as a standard for Pesticide detection. Useful in cannabis testing kits as a component of pesticide mixes (P698235).
Synthesis
General procedure for the synthesis of m-phenoxybenzyl bromide from 3-phenoxybenzyl alcohol: 3-phenoxybenzyl alcohol (2.09 g, 10.0 mmol) was dissolved in 18.7 mL of anhydrous dichloromethane and cooled to 0 °C. Subsequently, a solution of phosphorus tribromide (0.35 mL, 3.80 mmol) in 4.7 mL of dichloromethane was slowly added. The reaction mixture was naturally warmed to room temperature with continuous stirring for 30 minutes. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium bicarbonate and extracted with ether. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, purification by fast chromatography (eluent: hexane/ethyl acetate, 8:2) afforded 1.98 g of the target product, m-phenoxybenzyl bromide, as a colorless oil in 72% yield. The spectral data of the product were in agreement with those reported in the literature (Surman, MD; Mulvihill, MJ J. Org. Chem. 2002, 67, 4115-4121).
References
[1] Archiv der Pharmazie, 1983, vol. 316, # 7, p. 598 - 608
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 8, p. 3389 - 3395
[3] Patent: WO2008/110583, 2008, A1. Location in patent: Page/Page column 60
[4] Tetrahedron Letters, 1985, vol. 26, # 32, p. 3863 - 3866
[5] Journal of Organic Chemistry, 2002, vol. 67, # 12, p. 4115 - 4121
