m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 1797762Notes

Reaction equation

HRID 1797762 reaction equation
C(SCCNC(=O)CCN1C=CC=C1)C=C.[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23]O)=[O:22]>ClCCl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 60136134HCID 60136134, compound

Product 1

HCID 4473-Chlorobenzoic AcidYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-Allylsulfanyl-ethyl)-3-pyrrol-1-yl-propionamide (0.3704 g, 1.554 mmol, 1 equiv) was taken up in 100 ml of dichloromethane with stirring under nitrogen. The reaction mixture was cooled to between 0-4 C. Meta-chloroperoxybenzoic acid (0.4815 g, 2.790 mmol, 1.8 equiv) was added to the mixture and the reaction stirred at 0-4 C for 16 hours. The solvent was removed in vacuo and purification by flash chromatography on silica: eluting with ethyl acetate gave the by-product meta-chlorobenzoic acid. Further elution with the solvent mixture was gradually changed to a 1:1 ethyl acetate/ethanol gave the product which was isolated by removal of the solvent in vacuo as off-white crystals in 60% yield.

Workup

  1. temperatureThe reaction mixture was cooled to between 0-4 C
  2. stirringthe reaction stirred at 0-4 C for 16 hours
  3. customThe solvent was removed in vacuo and purification by flash chromatography on silica
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-bf937a21c427441e9d6260f0201adc71
Source dataset
uspto-grants-2013_01
Patent number
US08343212B2

Reaction notes

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