Benzenesulfenyl chloride → 2-(m-Chlorophenyl)-5-(phenylthio)thiophene

HRID 46646Notes

Reaction equation

HRID 46646 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:13]1([S:19]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Fe].C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([S:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11008040Benzenesulfenyl chloride2×HCID 123624442-(3-Chlorophenyl)thiophene

Product 1

HCID 203866072-(m-Chlorophenyl)-5-(phenylthio)thiopheneYield 22%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 89 g (0.46 mole) of 2-(m-chlorophenyl)thiophene, 400 ml of reagent carbon tetrachloride, 54 ml (67 g, 0.46 mole) of benzenesulfenyl chloride and 0.05 g of iron powder was allowed to stand for four days at room temperature. A further 12 ml (15 g, 0.10 mole) of benzenesulfenyl chloride and 0.05 g of iron powder were added. After four days the carbon tetrachloride was removed by distillation. The residue was distilled at reduced pressure to give 30 g (22%) of 2-(m-chlorophenyl)-5-(phenylthio)thiophene, b.p. 200°-205° C. (0.15 mm).

Workup

  1. customAfter four days the carbon tetrachloride was removed by distillation
  2. distillationThe residue was distilled at reduced pressure

Sources & evidence

ORD record
ord-e3cd56a17f6946528e527b3512c871fa
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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