反応 #44760

反応方程式

water

4-(benzyl)phenol

1-bromo-2-chloroethane

cesium carbonate

→

1-(2-chloroethoxy)-4-(benzyl)benzene

収率 86.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   温度at reflux for 12 hours
2. 2
   温度After cooling
3. 3
   抽出The mixture was extracted with ethyl acetate
4. 4
   洗浄The organic layer was washed with brine
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated under reduced pressure

実験手順

A solution of 4-(benzyl)phenol (638 mg, 3.46 mmol), 1-bromo-2-chloroethane (2.3 mL, 27.7 mmol) and cesium carbonate (4.5 g, 27.7 mmol) in 35 mL of acetonitrile was heated at reflux for 12 hours. After cooling, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 734 mg of 1-(2-chloroethoxy)-4-(benzyl)benzene, 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, 2H), 7.19 (dd, 1H), 7.18 (d, 2H), 7.12 (d, 2H), 6.85 (d, 2H), 4.21 (t, 2H), 3.93 (s, 2H), 3.80 (t, 2H) ppm.

出典