Water → HCID 18930439, compound

HRID 375177Notes

Reaction equation

HRID 375177 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([C:13]#[N:14])=[CH:10][C:9]=2[S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])=[CH:4][CH:3]=1.[Br:22]Br.O>O1CCOCC1>[Br:22][C:10]1[C:9]([S:15]([C:18]([F:19])([F:21])[F:20])(=[O:16])=[O:17])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:12][C:11]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24408Bromine2×HCID 18930422HCID 18930422, compound

Product 1

HCID 18930439HCID 18930439, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]pyrrole-2-carbonitrile (0.87 g, 0.0026 mol) in dioxane is cooled, treated with bromine (0.46 g, 0.00286 mol), stirred at room temperature for two hours, treated with additional bromine (0.21 g, 0.0013 mol), stirred overnight at room temperature, poured into water and extracted with ethyl acetate. The combined organic extracts are washed with water, saturated sodium meta-bisulfite solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a yellow syrup. Flash chromatography of the syrup using silica gel and a 1:4 ethyl acetate/hexanes solution gives the title product as a tan solid (0.27 g, mp 170°-185° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with water, saturated sodium meta-bisulfite solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow syrup

Sources & evidence

ORD record
ord-5d2a7f1fec0a4b04bc2df9c5f58371e3
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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