Sodium Cyanide → [4-(1,3-Benzoxazol-2-yl)-2-hydroxyphenyl]acetonitrile

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Reaction Conditions

Reaction Steps

The mixture of 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole (1.6 g, 3.8 mmol) and sodium cyanide (560 mg, 11.4 mmol) in DMF (10 mL) was stirred at 90° C. overnight. After cooling to rt, the mixture was diluted with EtOAc (100 mL), washed with H2O (2×50 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford the desired [4-(1,3-benzoxazol-2-yl)-2-hydroxyphenyl]acetonitrile as yellow solid. 1H NMR(CD3OD, 300 MHz), δ10.6(s, 1H), 7.8(m, 2H), 7.7(m, 2H), 7.5(d, 1H), 7.4(m, 2H). MS (ESI) 251 (M+H)+.

Provenance & Evidence