To a solution of 2-bromoethanol (3.5 mL, 49.3 mmol) in dichloromethane (DCM, 20 mL) was sequentially added tert-butyldimethylchlorosilane (TBDMSCl, 8.17 g, 54.2 mmol), triethylamine (Et3N, 13.85 mL, 98.6 mmol) and 4-dimethylaminopyridine (DMAP, 55 mg, 0.394 mmol). The reaction mixture was stirred at room temperature for 15 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was partitioned with 1N hydrochloric acid (HCl) and ethyl acetate (EtOAc). The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a yellow oily crude product. Purification by column chromatography (hexane as eluent) afforded the colorless oily product [(2-bromoethoxy)tert-butyldimethylsilane] (11.8 g, 49.3 mmol, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.89 (t, 2H), 3.40 (t, 2H), 0.91 (s, 9H), 0.091 (s, 6H); GC/MS (C8H19BrOSi) showed the molecular ion peak m/z 239 (M+).
