2-(4-Bromophenyl)thiophene → 2-(p-Bromophenyl)-5-(m-nitrophenylthio)thiophene

HRID 46650Notes

Reaction equation

HRID 46650 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]Cl)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:15][CH:14]=1>C(Cl)(Cl)(Cl)Cl.[Fe]>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[S:20][C:21]([S:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)=[CH:22][CH:23]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 70182982-(4-Bromophenyl)thiopheneHCID 156206861-(Chlorosulfanyl)-3-nitrobenzene

Product 1

HCID 203866592-(p-Bromophenyl)-5-(m-nitrophenylthio)thiopheneYield 44%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 21.2 g (0.112 mole) of m-nitrobenzenesulfenyl chloride in 160 ml of carbon tetrachioride were added 24.5 g (0.103 mole) of 2-(p-bromophenyl)thiophene and 0.1 g of iron powder. The reaction mixture was allowed to stand one week at room temperature. Evaporation of the solvent and recrystallization of the residue from 140 ml of ethyl acetate gave 17.6 g (44%) of 2-(p-bromophenyl)-5-(m-nitrophenylthio)thiophene, m.p. 120°-122° C.

Workup

  1. waitto stand one week at room temperature
  2. customEvaporation of the solvent and recrystallization of the residue from 140 ml of ethyl acetate

Sources & evidence

ORD record
ord-362563c75c84490c9f528892d920a28b
Source dataset
uspto-grants-1979_11
Patent number
US04174405

Reaction notes

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