2-(4-Methylphenyl)thiophene → 2-Phenylthio-5-p-tolylthiophene

HRID 46644Notes

Reaction equation

HRID 46644 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[CH:3][CH:2]=1.[C:13]1([S:19]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Fe].C(Cl)(Cl)(Cl)Cl>[C:13]1([S:19][C:9]2[S:8][C:7]([C:4]3[CH:5]=[CH:6][C:1]([CH3:12])=[CH:2][CH:3]=3)=[CH:11][CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 41284662-(4-Methylphenyl)thiopheneHCID 11008040Benzenesulfenyl chloride

Product 1

HCID 203866122-Phenylthio-5-p-tolylthiopheneYield 29%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Into 500 ml of reagent carbon tetrachloride were added 61 g (0.35 mole) of 2-p-tolylthiophene, 41 ml (51 g, 0.35 mole) of benzenesulfenyl chloride and 0.05 g of powdered iron. The reaction mixture was allowed to stand four days at room temperature after which the carbon tetrachloride was distilled off and the 45-gram residue washed with a mixture of 80 ml of ether and 250 ml of petroleum ether. Recrystallization of the washed solid from 300 ml of ethanol gave 28 g (29%) of 2-phenylthio-5-p-tolylthiophene, m.p. 85°-86° C.

Workup

  1. distillationafter which the carbon tetrachloride was distilled off
  2. washthe 45-gram residue washed with a mixture of 80 ml of ether and 250 ml of petroleum ether
  3. customRecrystallization of the washed solid from 300 ml of ethanol

Sources & evidence

ORD record
ord-ed9151af6c684116a96a15ba71897a85
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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