反応 #76341

反応方程式

3-(1,1,2,2-tetrafluoroethoxy)toluene

N-bromosuccinimide

→

3-(1,1,2,2-tetrafluoroethoxy)bromomethylbenzene

収率 96.0%

溶媒

carbon tetrachloride

反応条件

後処理

1. 1
   その他quenched with 300 mL of water
2. 2
   その他The organic layer was collected
3. 3
   洗浄washed with water and brine
4. 4
   乾燥dried over MgSO4
5. 5
   濃縮concentrated in vacuo

実験手順

Ex-628A) To a solution of 3-(1,1,2,2-tetrafluoroethoxy)toluene (50 g, 0.24 mol) and N-bromosuccinimide (42.75 g, 0.24 mol) in 100 mL of carbon tetrachloride under nitrogen was added 2,2′-azobisisobutyronitrile (0.71 g, 0.004 mol). The resultant mixture was refluxed for 2 h then cooled to room temperature and quenched with 300 mL of water. The organic layer was collected, washed with water and brine, dried over MgSO4, and concentrated in vacuo to give 66.0 g (96%) of the desired crude 3-(1,1,2,2-tetrafluoroethoxy)bromomethylbenzene product as a yellow oil. 1H NMR indicates that this oil is a mixture of products: 7% dibrominated, 67% monobrominated, and 20% starting material. The crude product was used without further purification. ESMS m/z=287 [M+H]+.

出典