1,2-Dibromoethane → 1-(2-Bromo-ethylsulfanyl)-2-trifluoromethyl-benzene
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[Br:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Br:12][CH2:13][CH2:14][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:1])([F:10])[F:11]Participants
7
Procedure
To a stirred solution of 2-(trifluoromethyl)thiophenol (2.96 ml, 22 mmol; CAS Reg. No. 13333-97-6) in DMF (65 ml) were added 1,2-dibromoethane (9.67 ml, 112 mmol) and potassium carbonate (3.41 g, 25 mmol). The reaction mixture was stirred for 2 h 30 min at ambient temperature. AcOEt (30 ml) and water (30 ml) were added and the layers were separated. The aqueous layer was extracted three times with AcOEt (3×20 ml). The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give the title compound as yellow oil (6.0 g, 22 mmol; quant.) which was sufficiently pure to be used in the next step.
Workup
- customthe layers were separated
- extractionThe aqueous layer was extracted three times with AcOEt (3×20 ml)
- washThe combined organic layers were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-3e39a79ec8c34e3f8ddb3a5b6f312470
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163793B2
Reaction notes
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