Water → 1-(3-bromophenyl)-2-(1H-pyrrol-3-yl)ethane-1,2-dione

Participants

Reaction Steps

To a solution of 3-[(3-bromophenyl)ethynyl]-1-(triisopropylsilyl)-1H-pyrrole (2.7 g, 8.5 mmol) in acetone (100 mml) is added a solution of MgSO4 (1.53 g, 12.75 mmol) and NaHCO3 (316 mg, 3.76 mmol) in water (50 ml), followed by the addition of KMnO4 (2.68 g, 17 mmol) in one portion at room temperature. After refluxing for 5 h, the reaction mixture is cooled to room temperature and extracted with ether (2×50 mL), the combined organic extracts are dried over MgSO4. The crude material is purified flash chromatography (silica gel, EtOAc/hexane:30/70 to 50/50) to afford the title compound as a yellow solid (42%). mp: 111-113° C. MS (−) ES: 276 (M−H)−.

Provenance & Evidence