Bromide ion → 2-(2-Bromo-5-methoxyphenyl)acetonitrile

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Reaction Steps

5-Methoxy-2-bromobenzyl bromide (72.8 g, 0.26 mol) is dissolved in EtOH (280 mL) and stirred at room temperature. Sodium cyanide (38.2 g, 0.78 mol) is dissolved in water and added to the solution of the bromide. The reaction mixture is heated to reflux temperature for 3 hours and then cooled to room temperature. Most of the ethanol is removed by rotary evaporator. A solid forms which is isolated by filtration and washed with water (500 mL). The crude material is purified using flash chromatography (CH2Cl2/hexanes, 1:1) to give 5-methoxy-2-bromophenylacetonitrile (53 g).

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