반응 #76341

반응 방정식

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

N-bromosuccinimide

→

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

수율 96.0%

용매

carbon tetrachloride

반응 조건

후처리

1. 1
   기타quenched with 300 mL of water
2. 2
   기타The organic layer was collected
3. 3
   세척washed with water and brine
4. 4
   건조dried over MgSO4
5. 5
   농축concentrated in vacuo

실험 절차

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]+.

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