22633-44-9

3296-90-0

22633-44-9

A. Synthesis of 3-bromomethyl-3-hydroxymethyl oxetane 2,2-Bis(bromomethyl)propane-1,3-diol (150 g, 0.573 mol) was dissolved in 650 mL of ethanol, followed by the slow addition of an ethanolic solution of sodium ethoxide (21%, 185.74 g, 0.573 mol) over 10 min. The reaction mixture was refluxed for 2 hours followed by stirring at room temperature for 16 hours. After completion of the reaction, the reaction mixture was filtered and the solvent was evaporated to give an oil containing solids. The crude product was dissolved in 200 mL of dichloromethane, filtered and the solvent was evaporated to give 98 g of crude 3-bromomethyl-3-hydroxymethoxetane. The crude product was purified by reduced pressure distillation (113°C, 3 mmHg) to give 52.95 g of pure product in 52% yield. NMR data: 1H NMR (δ, ppm): 3.75 (s, 2H), 3.88 (d, J = 4.9 Hz, 2H), 4.45 (s, 4H). 13C NMR (δ, ppm): 36.336 (t, J = 152.78 Hz), 45.0935 (s), 63.995 (t, J = 143.3 Hz), 77.216 (t, J = 152.78 Hz).