Iodoethane → 2-Ethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)butanenitrile

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Reaction Steps

To a solution of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile (2.0 g, 8.23 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (60 wt %, 1.2 g, 32.9 mmol) added portion wise. The mixture was stirred for 10 min and ethyl iodide (0.74 mL, 9.05 mmol) in THF (10 mL) was added. The mixture was stirred at room temperature for 12 h. The reaction mixture was quenched with water and diluted with ethyl acetate. The layers were separated and the organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and the residue purified by column chromatography (silica, 0-30% ethyl acetate/heptane) to afford the desired product (950 mg, 38%) as a brown solid: ESI MS m/z 300 [C18H26BNO2+H]+.

Provenance & Evidence