Water → bromodifluoromethyl phenyl sulfide

In a three-necked round-bottomed flask placed under a nitrogen atmosphere, topped with a dry-ice condenser and a dropping funnel, thiophenol (10.2 ml, 100 mmol) was added dropwise, over 40 min at 0° C., to a suspension of NaH (6 g, 150 mmol) in anhydrous DMF (100 ml). The mixture was then stirred at 0° C. for 30 min then cooled to −50° C. Dibromodifluoromethane (27 ml, 300 mmol) was then added at −50° C. The mixture was then stirred for 3 h at this temperature, then 30 min at ambient temperature. Water (100 ml) was added to the reaction mixture, then the product was extracted with ethyl ether (3×100 ml). The organic phases were washed with water (3×100 ml) and dried over MgSO4. After evaporation of the solvent, the residue was purified by distillation under reduced pressure (97° C./34 mmHg) to give the product [(bromodifluoromethyl)sulfanyl]benzene in the form of a colorless liquid (15.3 g, 60%).

1. customIn a three-necked round-bottomed flask placed under a nitrogen atmosphere
2. customtopped with a dry-ice condenser and a dropping funnel
3. temperaturethen cooled to −50° C
4. stirringThe mixture was then stirred for 3 h at this temperature
5. custom30 min
6. customat ambient temperature
7. extractionthe product was extracted with ethyl ether (3×100 ml)
8. washThe organic phases were washed with water (3×100 ml)
9. dry with materialdried over MgSO4
10. customAfter evaporation of the solvent
11. distillationthe residue was purified by distillation under reduced pressure (97° C./34 mmHg)

ORD record

ord-20c6b829fb3441be8d68afa03b466072

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853448B2