反応 #76392

反応方程式

4-bromophenol

4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-osylate

4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-tosylate

→

1-Bromo-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene

溶媒

DMF

cesium carbonate

反応条件

後処理

1. 1
   その他quenched with water
2. 2
   抽出extracted with ethyl acetate:hexane(1:1)
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   濃縮concentrated in vacuo
6. 6
   その他Purification by chromatography on silica gel (5% EtOAc/hexanes) eafforded 1-bromo-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene (47) a colorless oil (65%)

実験手順

To a solution of commercially available 4-bromophenol (46) (1 equi.) and 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-osylate (10) (1 equi.) in DMF (3 mL/mmole), cesium carbonate (1.25 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) eafforded 1-bromo-4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene (47) a colorless oil (65%).

出典