Benzoyl Peroxide → HCID 86619723, compound

Participants

Reaction Steps

To a mixture of 2-p-tolylisoindol-1,3-dione (A) (4.0 g, 17 mmol) and N-bromosuccinimide (3.0 g, 17 mmol) there were added carbon tetrachloride (70 mL) and benzoyl peroxide (8 mL) and the mixture was heated to the boil under halogen radiation over a period of 2 h. The resulting reaction solution was concentrated. The residue was stirred with chloroform (300 mL) with heating for 15 min and the mixture then filtered hot for isolation of the resulting solid matter. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (SiO2 (150 g) using cyclohexane/EtOAc 4:1 (2000 mL) as eluent). The bromide 2-(4-bromomethylphenyl)isoindol-1,3-dione (B) (4.1 g, 77%) was isolated as a white solid having a melting point of 191-199° C.

Provenance & Evidence