Potassium Carbonate → 1-(3-Bromopropylsulfanyl)-3,5-difluorobenzene

To a round-bottom flask was added 3,5-difluorobenzenethiol (4.9 g, 33.8 mmol) in ACN (50 mL). 3-Bromo-1-propanol (4.7 g, 34.0 mmol) and potassium carbonate (6.4 g, 46 mmol) were added, and the mixture was stirred at room temperature for 3 hours. The mixture was then filtered through a pad of Celite® and the solvent was removed under reduced pressure. The crude material was then dissolved in anhydrous DCM (100 mL). Triphenylphosphine dibromide (25 g, 59 mmol) was added to the mixture, which was then stirred for 2 hours. The solvent was removed under reduced pressure. The residue was suspended in EtOAc (200 mL), stirred for 1 hour, and filtered to remove solids. The filtrate was concentrated under reduced pressure, then diluted in 50% EtOAc/hexanes (200 mL), and filtered through a pad of Celite® and silica gel. The solution was then concentrated under reduced pressure to afford the title compound (5.8 g).

1. filtrationThe mixture was then filtered through a pad of Celite®
2. customthe solvent was removed under reduced pressure
3. dissolutionThe crude material was then dissolved in anhydrous DCM (100 mL)
4. stirringwas then stirred for 2 hours
5. customThe solvent was removed under reduced pressure
6. stirringstirred for 1 hour
7. filtrationfiltered
8. customto remove solids
9. concentrationThe filtrate was concentrated under reduced pressure
10. additiondiluted in 50% EtOAc/hexanes (200 mL)
11. filtrationfiltered through a pad of Celite® and silica gel
12. concentrationThe solution was then concentrated under reduced pressure

ORD record

ord-c349be7b045f4279933bc4dd74fe450c

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802856B2