Sodium Carbonate → 2-Bromo-4-pyridinecarboxaldehyde

Participants

Reaction Steps

A mixture of 21.0 g of 2-bromo-4-pyridinemethanol, 32.3 g of N-bromosuccinimide and 23.1 g of anhydrous sodium carbonate was suspended in 600 ml of benzene, and heated under reflux (bath temperature 110° to 120° C.) for 4 hours. The mixture was cooled over an ice bath, and a saturated aqueous solution of sodium hydrogen carbonate was added to adjust its pH to 9 to 10. The insoluble matter was removed by filtration (by washing with ethyl acetate). The organic layer was separated, washed with a 10% aqueous solution of sodium thiosulfate and then with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. The solvent was evaporated to give 18.2 g (yield 88%) of 2-bromo-4-pyridinecarboxaldehyde.

Provenance & Evidence