N-bromobutanimide → Ethyl 2-(bromomethyl)pyridine-3-carboxylate

Beteiligte Stoffe

Reaktionsschritte

Under a nitrogen atmosphere, ethyl 2-methylnicotinate (1.65 g, 10 mmol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (2.31 g, 13 mmol) and azoisobutyronitrile (164 mg, 1 mmol) were added thereto. The mixture was refluxed for 8 hours. After the completion of the reaction was confirmed by HPLC, the reaction mixture was allowed to cool down to a room temperature. The organic layer was washed with water 3 times and then with a saturated saline solution, and dried over magnesium sulfate. After the solvent was distilled off, the resulting residue was purified by flash column chromatography (Yamazen, Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=10:1) to give the title compound (1.45 g, 59.4%) as an oily substance.

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