4-Bromophenol → HCID 14026184, compound

To a cooled (0° C.) suspension of dry NaH (0.512 g, 21.4 mmol) in anhydrous DMF (10 mL) under an Argon atmosphere, a solution of 4-bromophenol (3.11 g, 17.8 mmol) in anhydrous DMF (20 mL) was added dropwise over 2-3 min. The mixture was stirred at 0° C. for 10 min and then allowed to warm to rt over 30 min. To the resulting white suspension was added 1-bromo-2-(2-methoxyethoxy)ethane (2.66 mL, 19.6 mmol) dropwise over 2 min and the mixture was stirred at rt for 30 min and then at 65° C. for 1.5 h. After cooling to rt, the mixture was concentrated under reduced pressure to an oily suspension, diluted with brine (80 mL), and the mixture was extracted with EtOAc (3×60 mL). The combined extracts were washed with brine (2×25 mL), dried over Na2SO4, filtered, and concentrated to give compound 85a as a mobile, pale amber-colored oil, used in the following reaction without further purification. Mass spectrum (LCMS, ESI pos.): Calcd. for C11H15BrO3, 275.0/277.0 (M+H). found 275.2/277.1