Reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:15]1([S:21]Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(SSC2C=CC=CC=2)C=CC=CC=1>[Fe].C(Cl)(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]([S:21][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]Participants
Procedure
Into 150 ml of reagent carbon tetrachloride were added 29 g (0.143 mole) 2-(p-isopropylphenyl)thiophene, 17 ml (21 g, 0.145 mole) of benzenesulfenyl chloride and 0.05 g of iron powder. At the end of four days a vapor phase chromatogram of the reaction mixture showed the presence of diphenyl disulfide, unreacted 2-(p-isopropylphenyl)thiophene and the desired product. An additional 4 ml (5 g, 0.035 mole) of benzenesulfenyl chloride and 0.05 g of iron powder was added and the mixture allowed to stand another four days at room temperature. Evaporation of the carbon tetrachloride gave a residue which was twice recrystallized from 250-ml portions of petroleum ether. There was obtained 16 g (36%) of 2-(p-isopropylphenyl)-5-(phenylthio)thiophene, m.p. 61°-63° C.
Workup
- customAt the end of four days
Sources & evidence
- ORD record
- ord-8f80ddcc91a040a0a30d4a6a80130775
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04174405
Linked notes
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