4-Bromo-2-fluorophenol → 4-Bromo-2-fluoro-1-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene

HRID 48106

반응식

HRID 48106 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[F:10][C:11]([F:38])([C:28]([F:37])([F:36])[C:29]([F:35])([F:34])[C:30]([F:33])([F:32])[F:31])[CH2:12][CH2:13][CH2:14][CH2:15]OC1(C)C=CC(S([O-])(=O)=O)=CC1>CN(C=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH2:14][CH2:13][CH2:12][C:11]([F:10])([F:38])[C:28]([F:36])([F:37])[C:29]([F:34])([F:35])[C:30]([F:31])([F:32])[F:33])=[C:4]([F:9])[CH:3]=1

참가 물질

5

반응물 2

HCID 27249814-Bromo-2-fluorophenolHCID 867593664-(5,5,6,6,7,7,8,8,8-Nonafluoro-octyloxy)-tosylate

생성물 1

HCID 206321684-Bromo-2-fluoro-1-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 10796Cesium carbonate용매

실험 절차

To a solution of commercially available 4-bromo-2-fluorophenol (25) (1 equi.) and 4-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-tosylate (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) and recrystallization from acetonitrile afforded 4-bromo-2-fluoro-1-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-benzene (26) a colorless oil (87%).

후처리

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography
  7. customon silica gel (5% EtOAc/hexanes) and recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-7621395f5351427bb19466a439f4e866
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703082B1

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