Benzenesulfenyl chloride → 2-p-Anisyl-5-(phenylthio)thiophene

HRID 46651Notes

Reaction equation

HRID 46651 reaction equation
[CH2:1]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:15]1([S:21]Cl)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)(Cl)Cl.[Fe]>[CH2:1]([C:10]1[S:11][C:12]([S:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11008040Benzenesulfenyl chlorideHCID 110309412-(4-Methoxybenzyl)thiophene

Product 1

HCID 203866452-p-Anisyl-5-(phenylthio)thiopheneYield 29%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 34 g (0.179 mole) of 2-p-anisylthiophene in 500 ml of carbon tetrachloride was treated with 23 ml (28.5 g, 0.197 mole) of benzenesulfenyl chloride and 0.1 g of iron powder. The mixture was allowed to stand at room temperature for eight days. The mixture was filtered to remove a small amount of solid. The filtrate was evaporated to give 67 g of crude solid product. Recrystallization from 220 ml of ethyl acetate gave 15.4 g (29%) of 2-p-anisyl-5-(phenylthio)thiophene, m.p. 92°-93° C.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove a small amount of solid
  3. customThe filtrate was evaporated
  4. customto give 67 g of crude solid product
  5. customRecrystallization from 220 ml of ethyl acetate

Sources & evidence

ORD record
ord-b702cd1924054e6f97e089e9f9f5781a
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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