Chloromethyl Methyl Ether → HCID 57173995, compound

Participants

Reaction Steps

To a slurry of sodium hydride (60% oily dispersion; 1.125 g, 28 mmol) in anhydrous DMF (80 mL), 1-(5-bromo-2-hydroxyphenyl)ethanone (4.67 g, 21.7 mmol) was added at 0° C. under a nitrogen atmosphere. After stirring for 1 h at the same temperature, methyl chloromethyl ether (tech, 90%; 2.35 g, 26 mmol) was added dropwise. The reaction mixture was allowed to gradually warm to room temperature and was stirred for 4 h. The reaction mixture was then quenched by pouring it onto saturated NH4Cl (aq) (100 mL). The reaction mixture was then extracted with 8:1 Et2O/EtOAc (2×150 mL). The combined organic layers were washed with water (4×80 mL), brine (60 mL), and dried over MgSO4. After purification by flash chromatography (9:1 hexane/EtOAc), the title compound (15) was obtained as colorless oil (4.44 g, 79% yield).

Provenance & Evidence