Methanol → 2-Bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene

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Reaction Conditions

Reaction Steps

The above-obtained [2-bromo-3,5-bis(methoxymethoxy)phenyl]methanol (3.5 g, 11 mmol) was dissolved in N,N-dimethylformamide (20 mL) and cooled to 0° C. The obtained solution was added with 60% sodium hydride-oil dispersion (0.59 g, 15 mmol) and benzyl bromide (2.0 mL, 17 mmol), followed by stirring at a room temperature for 1 hour. The reaction mixture was added with methanol and water and extracted with chloroform 3 times. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1 to 10/1) to obtain 2-bromo-1-(benzyloxymethyl)-3,5-bis(methoxymethoxy)benzene (3.2 g, 70%).

Provenance & Evidence