Benzoyl Peroxide → Methyl 2-(bromomethyl)-5-methylbenzoate

Participants

Reaction Steps

A light yellow, homogeneous solution of methyl 2,5-dimethylbenzoate (4.467 g, 27.2 mmol), 1-bromopyrrolidine-2,5-dione (4.84 g, 27.2 mmol) and benzoic peroxyanhydride (0.659 g, 2.72 mmol) in benzene (136 mL) under nitrogen was refluxed. After 8.5 hr, the reaction was cooled to room temperature. The succinimide was filtered, rinsed with benzene and the filtrate was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL) and washed with water (50 mL) and brine (50 mL), dried over MgSO4, and concentrated in vacuo to give crude product that was a mixture of the desired product and its regioisomer. This crude product was used in the next step without further purification.

Provenance & Evidence