Reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:5][C:4]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH2:23]([SH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:23]([S:30][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[S:5][C:4]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 3-(bromomethyl)-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 43, 0.100 g) and benzyl mercaptan (0.30 g) in acetonitrile (10 ml) was treated with potassium carbonate (0.46 g) and the mixture stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and water the organic layer as collected, dried over magnesium sulfate and concentrated. The residue was purified by SPE (Si cartridge) eluting initially with cyclohexane:chloroform (5:1) and then cyclohexane:chloroform (1:3) to give the title compound as a colourless oil.
Workup
- customThe reaction mixture was partitioned between ethyl acetate and water the organic layer
- customas collected
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by SPE (Si cartridge)
- washeluting initially with cyclohexane:chloroform (5:1)
Sources & evidence
- ORD record
- ord-dd4a8782106f4e99b7bf266d0a434e30
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091237B2
Linked notes
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