Benzoyl Peroxide → HCID 19698381, compound

Participants

Reaction Steps

A mixture of 4-nitro-3-trifluoromethanesulfonyloxytoluene (5.7 g, 20 mmol), N-bromosuccinimide (5.7 g, 32 mmol), and benzoyl peroxide (1 g) in carbon tetrachloride (75 mL) was refluxed for 18 h. The insoluble material formed was removed by filtration and the filtrate was concentrated. The residue was dissolved in DMF (40 mL) and potassium phthalimide (2.6 g, 14 mmol) was added. The mixture was stirred for 5 h at room temperature, poured into brine, and extracted with a 1:1 mixture of toluene and ethyl acetate. The organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 9:1 to 1:1 hexane/ethyl acetate to give 3.4 g of the title compound (39%).

Provenance & Evidence