Реакция #76392

Уравнение реакции

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

Растворители

DMF

cesium carbonate

Условия реакции

Обработка

1. 1
   Другоеquenched with water
2. 2
   Экстракцияextracted with ethyl acetate:hexane(1:1)
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried over MgSO4
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеPurification 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%)

Методика

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%).

Источник