Sodium periodate → N-(2-Fluoro-4-formylphenyl)methanesulfonamide

HRID 238938Notes

Reaction equation

HRID 238938 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=C)[CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12].I([O-])(=O)(=O)=[O:16].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:16])[CH:5]=[CH:4][C:3]=1[NH:10][S:11]([CH3:14])(=[O:13])=[O:12]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 69527926N-(4-Ethenyl-2-fluorophenyl)methanesulfonamide

Product 1

HCID 71418417N-(2-Fluoro-4-formylphenyl)methanesulfonamideYield 48%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of N-(2-Fluoro-4-vinylphenyl)methansulfonamide (20-2, 1.076 g, 5 mmol) in acetone and water (1:1, 20 mL) was treated with a catalytic amount of osmium tetroxide (4 wt % solution in hydroxyperoxide) and sodium periodate (2.139 g, 10 mmol). After being stirred at room temperature for 1 h, the mixture was concentrated into a small volume in vacuo. The residue was treated with aqueous sodium thiosulfate solution and then extracted with EtOAc several times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant to afford N-(2-Fluoro-4-formylphenyl)methanesulfonamide (20-3, LJO-326, 0.521 g, 48%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated into a small volume in vacuo
  2. additionThe residue was treated with aqueous sodium thiosulfate solution
  3. extractionextracted with EtOAc several times
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-1051948842494bcb96b302ef943834fa
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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