Benzoyl Peroxide → 6-(Bromomethyl)-2-phenylquinoline

Participants

Reaction Steps

A solution of 54 g of 2-phenyl-6-methyl-quinoline, 68 g of N-bromosuccinimide and 1.5 g of dibenzoyl peroxide in 700 ml of carbon tetrachloride is kept for 18 hours under reflux. Thereafter the reaction mixture is cooled to room temperature and the precipitate is filtered off. The filter residue is rinsed with carbon tetrachloride. The filtrate is evaporated and the residue is dissolved in ethyl acetate. This solution is washed with water and sodium chloride solution, dried over sodium sulphate and evaporated. The residue is taken up in 1.8 litres of ether and the insoluble constituents are filtered off. Concentration of the solution yields 2-phenyl-6-bromomethyl-quinoline of melting point 126°-127°C.

Provenance & Evidence