Nitric Acid → HCID 21876463, compound

HRID 1454714Notes

Reaction equation

HRID 1454714 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([CH3:12])(=O)=[O:10].S(=O)(=O)(O)O.[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][C:3]=1[S:9]([CH3:12])=[O:10]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 158897Benzene, 2,4-dichloro-1-(methylsulfonyl)-

Product 1

HCID 21876463HCID 21876463, compoundYield 74%

Conditions

Temperature
55 °C

Procedure

A mixture of (2,4-dichloro-phenyl)-methyl sulfone (Ono Mitsunori, Nakamura Yoshisada, Sato Shingo, Itoh Isamu, Chem. Lett, 1988, 395-398.; 3.33 g, 16 mmol) and sulfuric acid (conc, 14 ml) was added a mixture of sulfuric acid (4 ml) and nitric acid (fuming, 2 ml) dropwise under ice-water bath. The mixture was stirred at 55° C. for 1 h. The mixture was poured onto ice-water and neutralized with 6N aqueous NaOH and then extracted with dichloromethane. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with hexane/ethyl acetate (2:1/1:1) to give 3 g (74%) of the title compound as white solids.

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by flash chromatography
  7. washeluting with hexane/ethyl acetate (2:1/1:1)

Sources & evidence

ORD record
ord-0abbaacce0d343e58067e34699d086c4
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

Loading…