Acetone → N-Methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Participants

Reaction Steps

A round bottom flask was charged with Potassium carbonate (1.1 g, 8.1 mmol) and Acetone (40 mL, 500 mmol). To the suspension was added N-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide (2.0 g, 6.7 mmol) followed by Methyl iodide (0.50 mL, 8.1 mmol). The mixture was stirred at room temperature for 18 hours. The reaction was then diluted with dichloromethane (20 mL), filtered through a plug of diatomaceous earth, rinsed with dichloromethane and evaporated to a viscous oil. The material was subjected to high vacuum for 18 hours. The resulting white solid (2.00 g) was consistent for desired N-Methyl-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-methanesulfonamide and was used without further purification. 1H NMR (400 MHz, DMSO, d6) δ 7.63 (m, 1H), 7.60 (m, 1H), 7.49 (m, 1H), 3.24 (s, 3H), 2.97 (s, 3H), 1.30 (s, 12H).

Provenance & Evidence