反応 #7814

反応方程式

NaCN

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

DMF

H2O

→

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

溶媒

brine

反応条件

後処理

1. 1
   ろ過filtered
2. 2
   その他was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9)

実験手順

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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