N-bromobutanimide → 1-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene

HRID 392949노트

반응식

HRID 392949 반응식
[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:5])[F:4].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[F:1][C:2]([F:14])([O:6][C:7]1[CH:8]=[C:9]([CH2:13][Br:15])[CH:10]=[CH:11][CH:12]=1)[CH:3]([F:4])[F:5]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 74438Benzene, 1-methyl-3-(1,1,2,2-tetrafluoroethoxy)-

생성물 1

HCID 114603781-(Bromomethyl)-3-(1,1,2,2-tetrafluoroethoxy)benzene수율 96%

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

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]+.

후처리

  1. customquenched with 300 mL of water
  2. customThe organic layer was collected
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c71feb991cde4ee9896100630be5b207
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803388B2

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