Sodium Iodide → 6-bromo-8-methoxy-4H-benzo[1,3]dioxine

Participants

Reaction Steps

To a 450 ml solution of 50 g of 4-bromo-2-hydroxymethyl-6-methoxyphenol in DMF there was added 20 g of sodium hydride (60% mineral oil suspension) while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After then adding 15 ml of bromochloromethane and 3.2 g of sodium iodide to the reaction mixture, it was stirred at 80° C. for 6 hours under a nitrogen atmosphere. A saturated ammonium chloride aqueous solution was added to the reaction mixture and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane system) to obtain the target compound (31.2 g) as a colorless solid.

Provenance & Evidence