Methyl iodide → 2-Bromo-5-fluoroanisole

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Reaction Steps

In 15 ml of N,N-dimethylformamide were dissolved 3.94 g of 2-bromo-5-fluorophenol and 1.62 ml of methyl iodide, slowly added thereto was 5.08 g of potassium carbonate under ice-cooling. The mixture was stirred at room temperature for 3 hours. After insoluble matters were removed by filtration, distilled water was added to the filtrate, and the mixture was extracted with diethyl ether and washed with saturated brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography-(hexane:ethyl acetate=19:1→9:1), to give 4.10 g of 1-bromo4-fluoro-2-methoxybenzene.

Provenance & Evidence