Pyridine → 1-bromo-1,1,2,2-tetrafluorobutane

In the second step, a solution of 3-oxo-4,10-oxa-tricyclo[5,2,1,02,6]nonan-(8)9-ol (21.3 g, 125.0 mmol) in 200 mL acetonitrile was added to the 5-bromo-4,4,5,5-tetrafluoropentanoyl chloride solution. To the mixture was added 9.93 g (125.5 mmol) pyridine and the reaction was stirred at ambient temperature under nitrogen for 16 h. The solvent was removed under reduced pressure and the resulting oily residue was dissolved in 250 mL dichloromethane. The later solution was washed once with 200 mL 1 N HCl, washed once with 200 mL saturated aqueous NaHCO3, dried over MgSO4 and the solvent removed under reduced pressure to produce 3-oxo-4,10-oxa-tricyclo[5,2,1,02,6]nonan-(8)9-oxycarbonyl]-4-bromo-3,3,4,4-tetrafluorobutane as a white solid.

1. customThe solvent was removed under reduced pressure
2. dissolutionthe resulting oily residue was dissolved in 250 mL dichloromethane
3. washThe later solution was washed once with 200 mL 1 N HCl
4. washwashed once with 200 mL saturated aqueous NaHCO3
5. dry with materialdried over MgSO4
6. customthe solvent removed under reduced pressure

ORD record

ord-a6eb6d6cbd2a464783ab54a5a72d6def

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08956799B2