m-Chloroperbenzoic acid → HCID 53810667, compound

HRID 863395Notes

Reaction equation

HRID 863395 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][CH3:23])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>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[CH2:13][CH2:14]2)=[O:11])=[C:4]([CH2:21][S:22]([CH3:23])=[O:32])[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53996766HCID 53996766, compound

Product 1

HCID 53810667HCID 53810667, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[4-bromo-2-(methylsulphenylmethyl)phenyl]-3-cyclopropyl-2-(ethoxyiminomethyl)propan-1,3-dione (0.95 g) in dichloromethane cooled to -25° C. was slowly added m-chloroperbenzoic acid (50 to 60%, 0.55 g). The mixture was filtered in the cold and the filtrate diluted with ether and washed with 1M sodium metabisulphite, 25% sodium acetate and brine, dried (anhydrous sodium sulphate) and evaporated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate and hexane, giving as a yellow gum 1-[4-bromo-2-(methylsulphinylmethyl)phenyl]-3-cyclopropyl-2-(ethoxyiminomethyl)propan-1,3-dione (compound 8, 0.78 g), NMR (CDCl3) δ 1.0-1.4(7H, m), 2.55(3H, s), 2.8(1H, m), 4.0-4.2(4H, m), 7.2(1H, d), 7.5(1H, dd), 7.65(1H, d), 7.7(1H, bs).

Workup

  1. filtrationThe mixture was filtered in the cold and the filtrate
  2. additiondiluted with ether
  3. washwashed with 1M sodium metabisulphite, 25% sodium acetate and brine
  4. dry with materialdried (anhydrous sodium sulphate)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-9d15f70ff2ca48a1a73219bc8f1887d8
Source dataset
uspto-grants-1998_02
Patent number
US05721193

Reaction notes

Loading…