Bromine → 4-Bromo-2-Chloro-5-(5-Chloro-2-Thienyl)Pyrrole-3-Carbonitrile

HRID 374526Notes

Reaction equation

HRID 374526 reaction equation
[Br:1]Br.[Cl:3][C:4]1[NH:5][C:6]([C:11]2[S:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[CH:7][C:8]=1[C:9]#[N:10].CCCCCC.C(OCC)(=O)C>O1CCOCC1>[Br:1][C:7]1[C:8]([C:9]#[N:10])=[C:4]([Cl:3])[NH:5][C:6]=1[C:11]1[S:12][C:13]([Cl:16])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 152969642-Chloro-5-(5-Chloro-2-Thienyl)Pyrrole-3-CarbonitrileHCID 21226206Ethyl acetate hexane

Product 1

HCID 152969624-Bromo-2-Chloro-5-(5-Chloro-2-Thienyl)Pyrrole-3-Carbonitrile

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of bromine (0.70 g, 4.3 mmol) in p-dioxane is added dropwise to a solution of 2-chloro-5-(5-chloro-2-thienyl)pyrrole-3-carbonitrile (1.00 g, 4.1 mmol) in p-dioxane. The reaction mixture is stirred overnight at room temperature and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a (6:1) hexane/ethyl acetate solution gives the title product as a yellow solid, mp >200° C.

Workup

  1. concentrationconcentrated in vacuo
  2. customto obtain a residue

Sources & evidence

ORD record
ord-245b42fffe614d2e8498dc401ef66e5b
Source dataset
uspto-grants-1996_01
Patent number
US05480902

Reaction notes

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