Bromine → 5-Bromo-2-(p-chlorophenyl)-3-[(trifluoromethvl)sulfonyl]pyrrole

HRID 129619Notes

Reaction equation

HRID 129619 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][C:10]1[NH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[C:12]([S:13]([C:16]([F:17])([F:19])[F:18])(=[O:14])=[O:15])[CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 104480682-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole

Product 1

HCID 189304425-Bromo-2-(p-chlorophenyl)-3-[(trifluoromethvl)sulfonyl]pyrroleYield 24.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]pyrrole (1.0 g, 0.00323 mol) in chloroform is cooled, treated with a solution of bromine (0.52 g, 0.00323 mol) in chloroform, stirred at room temperature overnight, diluted with chloroform, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a dark syrup. Flash chromatography of the syrup using silical gel and a 1:5 ethyl acetate/hexanes solution gives the title product as an off-white solid (0.31 g, mp 73°-76° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a dark syrup

Sources & evidence

ORD record
ord-bc9265923da844d482747d0b1b77eb7b
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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