Hydrogen Peroxide → 5-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene

HRID 1844600Notes

Reaction equation

HRID 1844600 reaction equation
OO.[C:3]([C:7]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([O:15][CH3:16])=[C:11]([S:13][CH3:14])[CH:12]=1)([CH3:6])([CH3:5])[CH3:4].C(C1C=C([N+]([O-])=O)C([O:31]C)=C(C=1)N)(C)(C)C>C(O)(C(F)(F)F)C(F)(F)F>[C:3]([C:7]1[CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]([O:15][CH3:16])=[C:11]([S:13]([CH3:14])=[O:31])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 112068635-(tert-Butyl)-2-methoxy-3-nitroanilineHCID 584939295-Tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene

Product 1

HCID 584939515-Tert-butyl-1-methanesulphinyl-2-methoxy-3-nitro-benzene

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

At ambient temperature 1.1 ml of a 35% aqueous hydrogen peroxide solution are added to a solution of 500 mg 5-tert-butyl-2-methoxy-1-methylsulphanyl-3-nitro-benzene (may be obtained starting from 5-tert-butyl-2-methoxy-3-nitro-aniline analogously to the method described in Syn. Commun. 1984, 14, 215-8 or in Syn. Commun. 2001, 31, 1857-62) in 15 ml of 1,1,1,3,3,3-hexafluoroisopropanol. The solution is stirred for 5 h at ambient temperature and then quenched with 10% aqueous Na2S2O3 solution. The resulting mixture is extracted with ethyl acetate, and the combined extracts are washed with saturated aqueous NaHCO3 solution and saturated aqueous saline solution. The organic phase is dried (Na2SO4) and the solvent is distilled off. The residue is chromatographed on silica gel with petroleum ether/ethyl acetate (20:1) as eluant.

Workup

  1. custommay be obtained
  2. customquenched with 10% aqueous Na2S2O3 solution
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. washthe combined extracts are washed with saturated aqueous NaHCO3 solution and saturated aqueous saline solution
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. distillationthe solvent is distilled off
  7. customThe residue is chromatographed on silica gel with petroleum ether/ethyl acetate (20:1) as eluant

Sources & evidence

ORD record
ord-467c53eebe5d410a9028db23bf7b1fc1
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

Loading…