2-Methylquinoline → 2-(Bromomethyl)quinoline

Participants

Reaction Steps

To a solution of chinaldine (14.3 g, 0.1 mmol) and N-bromosuccinimide (17.8g, 0.1 mmol)in CCl4 (150 mL) was added benzoylperoxide (2.6 g, 0.025 mol) and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature and evaporated in vacuum. The residue was treated with 5% HBr solution, the precipitate was filtered offand the filtrate was treated with celite and then basified with NaHCO3solution. The product was extracted with ether and crystallized from petrolether to yield 2-(bromomethyl)-quinoline (2.8 g, 12.6%) as light tancrystals.

Provenance & Evidence