Sodium Bicarbonate → 2-Bromo-5-(dimethoxymethyl)pyridine

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Reaction Steps

To a solution of 2-bromo-5-pyridinecarboxaldehyde (1.02 g, 5.48 mmol) in methanol (100 mL) was added p-toluenesulfonic acid hydrate (1.05 g, 5.53 mmol), and the mixture was heated at reflux for 1.5 h. Diluted aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 2-bromo-5-dimethoxymethylpyridine (1.19 g, 94%) as an oil.

Provenance & Evidence