Tetrahydrofuran → 1-Bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene
Reaction equation
[CH2:1]([S-:3])[CH3:2].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1F.C1COCC1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:7]=1[S:3][CH2:1][CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.21 g of sodium ethanethiolate (80%) was added to a mixture of 0.55 g of l-bromo-2-fluoro-4-trifluoromethylsulfanylbenzene and 4 ml of THF under ice cooling, and the mixture was stirred at room temperature for 30 minutes. 2 mL of DMF was added to the reaction mixture, and the mixture was stirred at 80° C. for 2 hours. A saturated aqueous sodium bicarbonate solution was added to the cooled reaction mixture, and the mixture was extracted with ethyl acetate and then dried with anhydrous sodium sulfate. The mixture was concentrated under reduced pressure, and the resulting residue was applied to a silica gel column chromatography to obtain 0.37 g of 1-bromo-2-ethylsulfanyl-4-trifluoromethylsulfanylbenzene.
Workup
- stirringthe mixture was stirred at 80° C. for 2 hours
- extractionthe mixture was extracted with ethyl acetate
- dry with materialdried with anhydrous sodium sulfate
- concentrationThe mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-09172ec6784f44fda24172d803031bb5
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156838B2
Reaction notes
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