반응 #7814

반응 방정식

NaCN

2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole

DMF

H2O

→

[4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

용매

brine

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9)

실험 절차

A slurry of NaCN (435 mg, 8.9 mmol), 2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole (940 mg, 2.9 mmol), DMF (30 mL) and H2O (30 mL) was stirred at rt for 12 h. The reaction mixture was poured into brine (250 mL) and filtered. The resultant colorless solid was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.32 (s, 1H), 8.19 (dd, 1H), 7.77–7.80 (m, 1H), 7.70 (d, 1H), 7.59–7.61 (m, 1H), 7.38–7.41 (m, 2H), 3.92 (s, 2H). MS (ESI) 269 (M+H)+.

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