42186-06-1

The Journal of Organic Chemistry, 42, p. 3114, 1977 DOI: 10.1021/jo00439a002

Example 649 Synthesis of 2-(4-bromophenyl)propionitrile: 2-(4-bromophenyl)acetonitrile (5.0 g, 25.5 mmol) was dissolved in anhydrous THF (70 mL) and cooled to 0°C. Sodium hydride (60 wt%, 1.5 g, 38.3 mmol) was added batchwise under stirring. The reaction mixture was stirred at room temperature for 1 hour. Subsequently, methyl iodide (1.8 mL, 28.1 mmol) was added and stirring was continued for 14 hours. Upon completion of the reaction, the reaction was carefully quenched with water at 0 °C and diluted with ethyl acetate (200 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (silica gel, 0-30% ethyl acetate/heptane gradient elution) to afford the target product, 2-(4-bromophenyl)propionitrile (3.8 g, 72%), as a yellow oil.ESI MS m/z 210 [C9H8BrN + H]+.

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