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

HRID 558135

Reaction equation

HRID 558135 reaction equation
[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

Participants

6

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 2770Platinous chlorideCatalystHCID 16687962Silver hexafluoroantimonateCatalystHCID 111,2-DichloroethaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Conditions

Temperature
110 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-95ac991e75c34e8f80fa54d834ab4ec3
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Linked notes

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