m-Chloroperbenzoic acid → HCID 67072090, compound

HRID 852405Notes

Reaction equation

HRID 852405 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12](C(=O)C)=[C:11]([F:18])[CH:10]=1)([CH3:7])[CH3:6])[CH3:2].ClC1C=CC=[C:23]([C:27]([O:29]O)=[O:28])C=1>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:29][C:27](=[O:28])[CH3:23])=[C:11]([F:18])[CH:10]=1)([CH3:6])[CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 67072133HCID 67072133, compound

Product 1

HCID 67072090HCID 67072090, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 g (11.2 mmol) of 2-(4-acetyl-3-fluoro-phenoxy)-2-methyl-propionic acid ethyl ester in 30 ml dichloromethane was treated with 4.1 g (70%, 16.8 mmol) of 3-chloro perbenzoic acid. The reaction was stirred at RT. After 1 day additional 1.2 g (70%, 4.7 mmol), after 2 days 0.8 g (70%, 3.1 mmol) and after 3 days 0.6 g (70%, 2.3 mmol) of 3-chloro perbenzoic acid were added. The mixture was poured on ice/aqueous 10% disodium pyrosulfite solution and extracted with ether (three times). The organic phases were washed with aqueous 10% NaHCO3, aqueous saturated NH4Cl, aqueous 10% NaCl and dried over sodium sulfate to give 3.2 g of the title compound as light yellow oil.

Workup

  1. waitafter 2 days 0.8 g (70%, 3.1 mmol)
  2. additionThe mixture was poured on ice/aqueous 10% disodium pyrosulfite solution
  3. extractionextracted with ether (three times)
  4. washThe organic phases were washed with aqueous 10% NaHCO3, aqueous saturated NH4Cl, aqueous 10% NaCl
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-20b424b1f9bc4d8db0911c01fbb1d5ab
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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