Methyl 4-(chlorocarbonyl)benzoate → p-Methoxycarbonylphenyl 2-selenophenyl ketone

Participants

Reaction Steps

Selenophene (61) (5.0 g, 0.038 mole) and 4-methoxycarbonyl benzoyl chloride (62) (8.34 g, 0.042 mole) were dissolved in 50 ml of 1, 2-dichloroethane, and then anhydrous aluminum chloride (AlCl3) (10.19 g, 0.076 mole) was added. The mixture was heated under refluxing for 30 min, cooled, and quenched with 250 ml of icewater to stop the reaction. The organic layer was sequentially washed with water, 5% sodium carbonate solution, and water till neutral, then dried over MgSO4 and filtered. The solvent of the filtrate was evaporated under a reduced pressure, and the residue was subjected to a column chromatography (silica gel, chloroform), and then recrystallized from n-hexane to afford compound 63 in yellow crystals (4.78 g).

Provenance & Evidence