m-Chloroperbenzoic acid → 3-Bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)sulfinyl]pyrrole

HRID 375185Notes

Reaction equation

HRID 375185 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([S:7][C:8]([F:11])([F:10])[F:9])[NH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[CH:6]=[C:5]([S:7]([C:8]([F:11])([F:10])[F:9])=[O:24])[NH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 189304073-Bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole

Product 1

HCID 189304183-Bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)sulfinyl]pyrroleYield 50.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-2-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole (0.65 g, 0.00182 mol) in chloroform is cooled with an ice-water bath, treated with a solution of 3-chloroperoxybenzoic acid (0.52 g, 60% pure, 0.00182 mol) in chloroform, stirred for two hours, treated with saturated sodium metabisulfite solution, diluted with methylene chloride, washed with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a white solid. Flash chromatography of the solid using silica gel and a 1:10 ethyl acetate/hexanes solution gives the title product as a white solid (0.34 g, mp 177°-179° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. washwashed with saturated sodium hydrogen carbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto obtain a white solid

Sources & evidence

ORD record
ord-bdde30ff7e314ec8bf0b946637bb1aef
Source dataset
uspto-grants-1996_01
Patent number
US05484807

Reaction notes

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