Water → (4-Bromo-3-(difluoromethyl)phenyl)(ethyl)sulfane
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[CH:4][C:3]=1[CH:9]([F:11])[F:10].[CH2:12]([S-:14])[CH3:13].[Na+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:14][CH2:12][CH3:13])=[CH:4][C:3]=1[CH:9]([F:11])[F:10]Participants
5
Procedure
1-Bromo-2-(difluoromethyl)-4-fluorobenzene (Preparation 50, 772 mg, 3.43 mmol) and sodium ethanethiolate (352.7 mg, 3.77 mmol) in DMSO (5 mL) was heated at 50° C. for 18 hours. On cooling, water (70 mL) was added to the reaction mixture, the product was extracted with EtOAc (20 mL×3). The combined organic layers were concentrated to give the crude product, which was purified by silica gel column chromatography eluting with heptane to afford the title compound as a colourless oil (260 mg, 28%).
Workup
- temperatureOn cooling
- extractionthe product was extracted with EtOAc (20 mL×3)
- concentrationThe combined organic layers were concentrated
- customto give the crude product, which
- customwas purified by silica gel column chromatography
- washeluting with heptane
Sources & evidence
- ORD record
- ord-89e88194f2824ebc84ffce6e64c82f06
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952008B2
Reaction notes
Loading…