Benzoyl Peroxide → 2-Bromo-5-(methoxymethyl)-1,3-dimethylbenzene

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2-bromomesitylene (5.00 g) was dissolved in carbon tetrachloride (50 mL). NBS (4.45 g) and benzoyl peroxide (182 mg) were added to the solution, and the mixture was stirred at 80° C. for three hours. The reaction mixture was returned to room temperature and filtered. The solid collected by filtration was washed with n-heptane. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-heptane). The resulting fraction was concentrated under reduced pressure. The residue was dissolved in THF (120 mL). Sodium methoxide (28% solution in methanol, 9.35 mL) was added to the solution, and the mixture was stirred at 80° C. for four hours. The reaction mixture was returned to room temperature and concentrated under reduced pressure. Water was added to the residue, followed by extraction with DCM. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 0% to 5%). The resulting fraction was concentrated under reduced pressure, and the residue was purified again by NH silica gel column chromatography (n-heptane) to give the title compound (880 mg).

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