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

HRID 1975191Notes

Reaction equation

HRID 1975191 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-2ba629dbd7c44a7ca94f5dfb1b15ccba
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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