2-Phenylthiophene → 2-(p-Chlorophenylthio)-5-phenylthiophene

HRID 46652

Reaction equation

HRID 46652 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]Cl)=[CH:15][CH:14]=1>C(Cl)(Cl)(Cl)Cl.[Fe]>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:9]2[S:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:11][CH:10]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 699992-PhenylthiopheneHCID 110844654-Chlorobenzenesulfenylchloride

Product 1

HCID 203866392-(p-Chlorophenylthio)-5-phenylthiopheneYield 53%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 40 g (0.250 mole) of 2-phenylthiophene in 200 ml of carbon tetrachloride was treated at room temperature with 45 g (0.252 mole) of p-chlorobenzenesulfenyl chloride. Iron powder (0.1 g) was added and the reaction mixture was allowed to stand for seven days at room temperature. Filtration removed a small amount of insoluble material. Evaporation of the filtrate gave a residue of 79.8 g of crude product, m.p. 85°-87° C. Recrystallization of the residue from 400 ml of absolute ethanol gave 40 g (53%) of 2-(p-chlorophenylthio)-5-phenylthiophene, m.p. 101°-103° C.

Workup

  1. filtrationFiltration
  2. customremoved a small amount of insoluble material
  3. customEvaporation of the filtrate
  4. customgave a residue of 79.8 g of crude product, m.p. 85°-87° C
  5. customRecrystallization of the residue from 400 ml of absolute ethanol

Sources & evidence

ORD record
ord-d5c59490776b453cb09e597f887af620
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Linked notes

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