N-bromobutanimide → Methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate

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Reaction Steps

10.8 g (0.045 mol) of methyl 2,3-dimethyl-4-methanesulfonylbenzoate was dissolved in 80 ml of carbon tetrachloride, and 8.3 g (0.047 mol) of N-bromosuccinimide and 0.1 g of benzoyl peroxide were then added, followed by stirring for 3 hours under heating reflux. After the solution was allowed to cool, insoluble substance was removed by filtration, and the resulting filtrate was washed with an aqueous sodium hydrogen bisulfite solution, and then dried over anhydrous magnesium sulfate. Next, the solvent was distilled off under reduced pressure, the residue was purified through silica gel column chromatography to obtain 6.2 g of methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate in a state of crystals. Yield=43.4%.

Provenance & Evidence