m-Chloroperbenzoic acid → 3-Bromo-5-(p-chlorophenyl)-2-[(trifluoromethyl)sulfinyl]-4-[(trifluoromethyl)sulfonyl]pyrrole

HRID 129639Notes

Reaction equation

HRID 129639 reaction equation
[Br:1][C:2]1[C:6]([S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[NH:4][C:3]=1[S:21][C:22]([F:25])([F:24])[F:23].ClC1C=C(C=CC=1)C(OO)=[O:31].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[C:6]([S:7]([C:10]([F:11])([F:12])[F:13])(=[O:8])=[O:9])=[C:5]([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[NH:4][C:3]=1[S:21]([C:22]([F:25])([F:24])[F:23])=[O:31]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 189303903-Bromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]-2-[(trifluoromethyl)thio]pyrrole

Product 1

HCID 189304413-Bromo-5-(p-chlorophenyl)-2-[(trifluoromethyl)sulfinyl]-4-[(trifluoromethyl)sulfonyl]pyrroleYield 60.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]-2-[(trifluoromethyl)thio]pyrrole (0.4 g, 0.00082 mol) in chloroform (5 mL) is cooled with an ice bath, treated with a solution of 3-chloroperoxybenzoic acid (0.24 g, 60%, 0.00082 mol) in chloroform (10 mL), stirred for two hours, warmed to room temperature and stirred overnight. The reaction mixture is 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 residue. The residue is placed on a prep plate and eluted with a 1:2 ethyl acetate/hexanes solution to give the title product as a white solid (0.25 g, mp 120°-170° C.) which is identified by 1HNMR spectral analysis.

Workup

  1. stirringstirred overnight
  2. washwashed with saturated sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a residue
  6. washeluted with a 1:2 ethyl acetate/hexanes solution

Sources & evidence

ORD record
ord-dbbdfbb02434455882e8483a4632a258
Source dataset
uspto-grants-1995_11
Patent number
US05468877

Reaction notes

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