m-Chloroperbenzoic acid → HCID 53765258, compound

HRID 863396Notes

Reaction equation

HRID 863396 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH:9]([CH:15]=[N:16][O:17][CH2:18][CH3:19])[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[C:4]([CH2:21][S:22]([CH3:24])=[O:23])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH:9]([CH:15]=[N:16][O:17][CH2:18][CH3:19])[C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[C:4]([CH2:21][S:22]([CH3:24])(=[O:33])=[O:23])[CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 53810667HCID 53810667, compound

Product 1

HCID 53765258HCID 53765258, compoundYield 2.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-[4-bromo-2-(methylsulphinylmethyl)phenyl]-3-cyclopropyl-2-(ethoxyiminomethyl)propan-1,3-dione (350 mg) and m-chloroperbenzoic acid (50-60%, 400 mg) in dichloromethane was stirred at room temperature for one hour. 1M sodium metabisulphite was added and the mixture cooled to 0° C. and filtered. The filtrate was diluted with ether, washed with 25% sodium acetate and brine, dried (anhydrous sodium sulphate) and evaporated. The residue was purified by column chromatography on silica gel, eluting with acetone and hexane, giving as a brown gum 1-[4-bromo-2-(methylsulphonylmethyl)phenyl]-3-cyclopropyl-2-(ethoxyiminomethyl)propan-1,3-dione (compound 9, 10 mg), NMR (CDCl3) δ 1.0-1.2(7H, m), 2.45(1H, m), 2.8(3H, s), 4.05(2H, q), 4.6(2H, q), 7.5-7.6(2H, m), 7.65-7.7(2H, m)

Workup

  1. temperaturethe mixture cooled to 0° C.
  2. filtrationfiltered
  3. additionThe filtrate was diluted with ether
  4. washwashed with 25% sodium acetate and brine
  5. dry with materialdried (anhydrous sodium sulphate)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with acetone and hexane

Sources & evidence

ORD record
ord-c3e9f80b2b84438fb2a7099c0766d158
Source dataset
uspto-grants-1998_02
Patent number
US05721193

Reaction notes

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