1-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol → 2-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan

HRID 558135

반응식

HRID 558135 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:14])[CH2:10][CH2:11][CH2:12]O>ClCCCl.C(Cl)(Cl)Cl.CC(O)C.F[Sb-](F)(F)(F)(F)F.[Ag+].[Pt](Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][CH2:11][CH2:12][O:14]1

참가 물질

6

반응물 1

HCID 574450901-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol

생성물 1

HCID 574450912-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan수율 77.3%

시약·촉매·용매 4

HCID 2770Platinous chloride촉매HCID 16687962Silver hexafluoroantimonate촉매HCID 111,2-Dichloroethane용매HCID 21906603Chloroform isopropyl alcohol용매

반응 조건

온도
110 °C

실험 절차

Combine 1-(2-bromo-4-fluoro-phenyl)-butane-1,4-diol (1 g, 3.8 mmol), silver (I)hexafluoroantimonate (131 mg, 0.4 mmol), platinum(II) chloride (40 mg, 0.2 mmol) in 1,2-dichloroethane (10 mL) in a pressure tube. Seal the tube and heat the mixture overnight at 110° C. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (20% ethyl acetate in hexane) to give the title compound as a pale yellow oil (0.72 g, 77%).

후처리

  1. customSeal the tube
  2. washWash the organic phase with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-95ac991e75c34e8f80fa54d834ab4ec3
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063035B2

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