Triphenylphosphine → 4-(Aminomethyl)-3-chlorobenzonitrile

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To a solution of 2-choro-4-cyanobenzyl azide (5.8 g, 30.1 mmol) in THF/H2O (3:1), was added triphenyl phosphine (12.3 g, 46.7 mmol). The reaction was stirred at room temperature overnight, then neutralized with 1N sodium hydroxide, extracted with ethyl acetate (150 ml×3). The organic layer was dried over sodium sulfate, and then solvent was removed in vacuo. The product was purified by silica-gel chromatography column with methanol/ammonia hydroxide/ethyl acetate (20:1:69) to give 4.5 g (90%) of 2-chloro-4-cyanobenzylamine. NMR (CDCl3): δ 4.0 (s, 2H, CH2), 7.58 (d, 2H, HAr), 7.62 (s, 1H, HAr)

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