m-Chloroperbenzoic acid → HCID 18930426, compound

HRID 1975207Notes

Reaction equation

HRID 1975207 reaction equation
[Br:1][C:2]1[NH:3][C:4]([S:15][C:16]([F:19])([F:18])[F:17])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:6]=1[Br:7].ClC1C=C(C=CC=1)C(OO)=[O:25]>C(Cl)(Cl)Cl>[Br:1][C:2]1[NH:3][C:4]([S:15]([C:16]([F:19])([F:18])[F:17])=[O:25])=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:6]=1[Br:7]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18930417HCID 18930417, compound

Product 1

HCID 18930426HCID 18930426, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,3-dibromo-4-(p-chlorophenyl)-5-[(trifluoromethyl)thio]pyrrole (1.0 g, 0.0023 mol) in chloroform (10 mL) is treated with 3-chloroperoxybenzoic acid (0.4 g, 60%, 0.0023 mol) with stirring at 0° C., warmed to room temperature with stirring for two hours, washed with saturated sodium metabisulfite solution, saturated sodium hydrogen carbonate solution, water 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 yellow solid (0.4 g, mp 165.5°-167.5° C.) which is identified by 1NHMR, 19FNMR and 13CNMR spectral analyses.

Workup

  1. temperaturewarmed to room temperature
  2. stirringwith stirring for two hours
  3. washwashed with saturated sodium metabisulfite solution, saturated sodium hydrogen carbonate solution, water 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-2c10bdb9417e43cb9e3b3003fb8ba218
Source dataset
uspto-grants-1994_02
Patent number
US05284863

Reaction notes

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