2-Phenylthiophene → 2-Phenyl-5-(phenylthio)thiophene

HRID 46643

Reaction equation

HRID 46643 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.[C:12]1([S:18]Cl)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Fe].C(Cl)(Cl)(Cl)Cl>[C:1]1([C:7]2[S:8][C:9]([S:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 699992-PhenylthiopheneHCID 11008040Benzenesulfenyl chloride

Product 1

HCID 203867042-Phenyl-5-(phenylthio)thiopheneYield 17.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

In a 500 ml flask were placed 36.9 g (0.23 mole) of 2-phenylthiophene, 200 ml of reagent carbon tetrachloride, 36.9 g (0.26 mole) of benzenesulfenyl chloride and 0.2 g of iron powder. The reaction mixture was allowed to stand four days at room temperature. Distillation of the carbon tetrachloride gave a crystalline residue which was recrystallized first from ethanol-ethyl acetate (9:1) and then from ethyl acetate-pentane (1:9) to give 10.6 g (17%) of 2-phenyl-5-(phenylthio)thiophene, m.p. 72.5°-74.5° C.

Workup

  1. customIn a 500 ml flask were placed
  2. distillationDistillation of the carbon tetrachloride
  3. customgave a crystalline residue which
  4. customwas recrystallized first from ethanol-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-f02972133e9b4fe0a5e9eac8f921a27f
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Linked notes

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