Water → 2-(4-Bromo-2-methylphenyl)-2-methylpropanenitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(4-bromo-2-methylphenyl)acetonitrile (3.93 g, 18.8 mmol) in anhydrous DMF (35 mL) is added methyl iodide (2.45 mL, 39.4 mmol). The solution is cooled to 0° C. and sodium hydride (60% susp. in oil, 1.47 g, 61.1 mmol) is added in 3 equal portions over 20 min. The reaction mixture is then left stirring and slowly warmed up to room temperature for 18 h. The solution turned to a thick brown-orange paste. At 0° C., water (50 mL) is then slowly added and the solution is extracted with a 2:1 solution of hexane/Et2O (3×50 mL). The organic layer is washed with brine, dried with MgSO4, filtered and concentrated under reduced pressure. The crude is purified by flash-chromatography, eluting with hexane/EtOAc (9:1) to provide the expected product 2-(4-bromo-2-methylphenyl)-2-methylpropanenitrile (3.1 g, 66%) as a clear yellowish oil. 1H NMR (300 MHz, CHLOROFORM-D): δ 7.40-7.30 (2H, m), 7.16 (2H, d, J=8.5 Hz), 2.63 (3H, s), 1.77 (6H, s).

Provenance & Evidence