Hydrogen Bromide → HCID 57939700, compound

Temperature

60 °C

A 250 mL round bottom flask equipped with a condenser was charged with 3.22 g (27.3 mmol) (S)-4-fluoromethyl-dihydro-furan-2-one. 16 mL (91 mmol) hydrobromic acid (33% in acetic acid) was added in one portion and the mixture was stirred at 60° C. for 45 minutes. A second portion of 16 mL (91 mmol) hydrobromic acid (33% in acetic acid) was added and stirring was continued at the same temperature for an additional 45 minutes, whereupon 96 mL ethanol were added. The resulting mixture was stirred at 60° C. for 65 minutes. The solvent was evaporated under reduced pressure (90 mbar) and the residue was dissolved in 300 mL toluene. The organic solution was washed with 300 mL saturated aqueous NaHCO3 and 300 mL water. Following drying over Na2SO4, filtration and evaporation of the solvent, the crude mixture was distilled under reduced pressure (82° C./1 mbar) to give 3.96 g product (64%; assay 98.9%).

1. customA 250 mL round bottom flask equipped with a condenser
2. stirringstirring
3. additionwere added
4. stirringThe resulting mixture was stirred at 60° C. for 65 minutes
5. customThe solvent was evaporated under reduced pressure (90 mbar)
6. dissolutionthe residue was dissolved in 300 mL toluene
7. washThe organic solution was washed with 300 mL saturated aqueous NaHCO3 and 300 mL water
8. dry with materialFollowing drying over Na2SO4, filtration and evaporation of the solvent
9. distillationthe crude mixture was distilled under reduced pressure (82° C./1 mbar)

ORD record

ord-be9bc0d726084f49a6662dfd38603aba

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07619101B2