Acetone → 1-(2-Iodoethyl)adamantane

Participants

Reaction Steps

To a solution of 2-adamantylethyl 4-bromobenzenesulfonate (Preparation 92, 1.0 g, 2.5 mmol) in acetone (25 ml) was added sodium iodide (0.75 g, 5 mmol) and the reaction mixture was left to stir at room temperature for 72 h. The resulting precipitate was filtered and the filtrate was diluted with water (100 ml) and extracted with dichloromethane (100 ml). The extract was washed with brine (100 ml), dried (MgSO4) and concentrated in vacuo to give the title compound as a white crystalline solid (0.54 g, 75%).

Provenance & Evidence