Benzoyl Peroxide → Ethyl 2-bromomethyl-6-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

19.56 g of N-bromosuccinimide and 4.84 g of benzoyl peroxide were added to a solution of 19.40 g of ethyl 2-methoxy-6-methylbenzoate in 150 ml of carbon tetrachloride. The reaction medium was refluxed for 6 hours (no further change). The reaction medium was cooled to 5° C. and the succinimide was filtered. The organic phase was washed with a saturated sodium hydrogen carbonate solution (2×150 ml), dried over magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel (column puriFlash, IR-50SI/800G, Spot II) eluted with heptane/ethyl acetate (gradient). 15.5 g of ethyl 2-bromomethyl-6-methoxybenzoate were obtained in the form of a yellow oil which later crystallizes. Yield=56%.

Provenance & Evidence