Iodine → (2-Hydroxymethylphenyl)acetonitrile

Participants

Reaction Steps

To a suspension of sodium borohydride (454 mg, 12.0 mmol) in THF (20 mL) was slowly added a solution of 2-cyanomethylbenzoic acid (1.61 g, 10.0 mmol) in THF (20 mL), then a solution of iodine (1.30 g, 5.0 mmol) in THF (20 mL) was slowly added at rt. The resulting mixture was stirred at rt for 1 h. The reaction was quenched with 3 N HCl (10 mL), then extracted with Et2O (3×20 mL). The combined organic phases were washed with brine (20 mL), and dried over anhydrous sodium sulfate. The residue was purified by silica gel chromatography (Hex:EtOAc=80:20→60:40) to give the title compound as a yellow oil. 1H NMR (CD3OD): δ=3.98 (s, 2H), 4.27 (s, 2H), 7.33 (m, 2H), 7.41 (m, 2H).

Provenance & Evidence