m-Chloroperbenzoic acid → HCID 59540594, compound

HRID 1677537Notes

Reaction equation

HRID 1677537 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:15][CH2:14]S[CH2:12][CH2:11]2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[S:27](S([O-])=O)([O-:30])(=O)=[O:28].[Na+].[Na+]>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:11][CH2:12][S:27](=[O:30])(=[O:28])[CH2:14][CH2:15]2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 59540645HCID 59540645, compound

Product 1

HCID 59540594HCID 59540594, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalyst2×HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-(3-bromo-5-methoxy-phenyl)-thiomorpholine (239 mg, 0.83 mmol) in methylene chloride (10 ml) and methanol (5 drops) was added m-CPBA (409 mg, 1.83 mmol). After 1 hour methanol (10 drops) was added to enhance solubility. The mixture was stirred another 3 hours. Methylene chloride (25 ml) and a 10% solution of aqueous sodium metabisulfite (35 ml) were added and the material was shaken in a reparatory funnel. The organic phase was collected and washed consecutively with equal volumes of 5% aqueous sodium bicarbonate and then brine solution. The aqueous phases were back-extracted with methylene chloride (2×25 ml), the organic phases combined, dried (MgSO4), filtered and stripped to a crude residue. The material was loaded onto 2 preparative TLC plates, eluting with 40% ethyl acetate in hexanes. The product band was collected to afford 76 mg of 4-(3-bromo-5-methoxy-phenyl)-thiomorpholine 1,1-dioxide as a off-white solid.

Workup

  1. stirringthe material was shaken in a reparatory funnel
  2. customThe organic phase was collected
  3. washwashed consecutively with equal volumes of 5% aqueous sodium bicarbonate
  4. extractionThe aqueous phases were back-extracted with methylene chloride (2×25 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. washeluting with 40% ethyl acetate in hexanes
  8. customThe product band was collected

Sources & evidence

ORD record
ord-232f2e54654d49c6bb6d4d3c72260755
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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