Reaction #645317

Reaction equation

1-(2-bromo-4-fluoro-phenyl)-butane-1,4-diol

→

title compound

Yield 77.3%

2-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan

Yield 77.3%

Solvents

1,2-dichloroethane

chloroform IPA

Conditions

Workup

1. 1
   OtherSeal the tube
2. 2
   WashWash the organic phase with aqueous saturated sodium chloride and water
3. 3
   DryingDry the mixture over sodium sulfate
4. 4
   ConcentrationConcentrate the solution in vacuo
5. 5
   OtherPurify by column chromatography (20% ethyl acetate in hexane)

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%).

Source