Dimethylformamide → 2-Bromo-5-[(cyclobutyloxy)methyl]-1,3-dimethoxybenzene

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Reaction Steps

To a mixture of cyclobutyl alcohol (4.16 g, 57.7 mmol) and DMF (30 mL) was added sodium hydride (60% dispersion in oil: 2.31 g, 57.7 mmol) while cooling on ice, and the mixture was stirred at room temperature for 1 hour. To this mixture was slowly added dropwise a mixture of 2-bromo-5-(chloromethyl)-1,3-dimethoxybenzene (2.47 g, 9.3 mmol) and DMF (30 mL), and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the mixture while cooling on ice, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1) to obtain the title compound (2.39 g, 7.94 mmol).

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