Benzoyl Peroxide → methyl 2-bromomethyl-1-naphthoate

Participants

Reaction Steps

N-Bromosuccinimide (0.748 g) was added to a solution of methyl 2-methylnapthalene-1-carboxylate (0.7 g) in acetonitrile (30 ml) and the mixture was heated to reflux. Benzoyl peroxide (0.093 g) was added and the reaction mixture was heated at reflux for 4 hours. After cooling, ethyl acetate was added and the solution was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM and pentane with a gradient of 7.5-25% to give methyl 2-bromomethylnaphthalene-1-carboxylate (0.529 g) as a yellow solid.

Provenance & Evidence