Synthesis
General procedure for the synthesis of isopropyl-2-bromoethyl ether from isopropoxyethanol: 2-isopropoxyethanol (2 mL, 17.34 mmol) was added to a 2-necked flask equipped with a reflux condenser, a magnetic stirring bar and a septum. Phosphorus tribromide (0.52 mL, 5.45 mmol) was added slowly dropwise via syringe. The temperature increased and slight reflux occurred during the reaction. The reaction mixture was stirred under argon protection at room temperature for 24 hours. Upon completion of the reaction, the reaction was quenched with water and extracted with hexane. The organic layers were combined, dried over anhydrous magnesium sulfate and subsequently concentrated to afford 1 g (34% yield) of the target product, isopropyl-2-bromoethyl ether, as a colorless oil. The product was characterized by 1H NMR (CDCl3): δ 3.78 (t, 2H); 3.61 (m, 1H); 3.42 (t, 2H); 1.18 (d, 6H).
References
[1] Patent: US2007/219212, 2007, A1. Location in patent: Page/Page column 21
[2] Journal of the American Chemical Society, 1934, vol. 56, p. 127
[3] Zeitschrift fuer Physikalische Chemie, Abteilung A: Chemische Thermodynamik, Kinetik, Elektrochemie, Eigenschaftslehre, 1940, vol. 185, p. 91
[4] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1007 - 1012
