Water → HCID 68062528, compound

Participants

Reaction Steps

To a solution of 4-methyl-N-(methylsulfonyl)benzamide (Preparation 55, 550 mg, 2.58 mmol) in tetrachloromethane (10 mL) was added N-bromosuccinimide (459 mg, 2.58 mmol) and diphenylperoxyanhydride (62.5 mg, 0.258 mmol) and the mixture was heated at reflux under nitrogen for 4 hours. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with DCM (50 mL). The organic layer was dried over magnesium sulphate and evaporated in vacuo to yield a cream solid. The solid was re-dissolved in trichloromethane (10 mL), diphenylperoxyanhydride (62 mg, 0.25 mmol) and N-bromosuccinimide (300 mg, 1.69 mmol) were added and the mixture heated at reflux for 6 hours then cooled to room temperature and evaporated in vacuo. The resulting residue was partitioned between DCM (50 mL) and water (50 mL), the aqueous further extracted with DCM (50 mL) and the combined organics dried over magnesium sulphate and concentrated in vacuo to yield a cream solid (625 mg). A portion of this material was purified by silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound as a white solid (25 mg).

Provenance & Evidence