2-Chloro-5-((4-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamide → 2-Chloro-5-(4-fluoro-benzoyl)-benzenesulfonamide

HRID 1515415Notes

Reaction equation

HRID 1515415 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[OH:9])=[CH:4][C:3]=1[S:17]([NH2:20])(=[O:19])=[O:18].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[CH:4][C:3]=1[S:17]([NH2:20])(=[O:18])=[O:19]

Participants

5

Reactant 2

HCID 581074952-Chloro-5-((4-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamideHCID 131709961Jones' reagent

Product 1

HCID 581074432-Chloro-5-(4-fluoro-benzoyl)-benzenesulfonamideYield 74.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 65 mg of 2-chloro-5-((4-fluoro-phenyl)-hydroxy-methyl)-benzenesulfonamide in 1 mL of acetone is stirred at room temperature as 0.2 mL of 3 M Jones' reagent is added. The reaction mixture is stirred at room temperature for 30 minutes then diluted with ethyl acetate, filtered through celite, the filtrate is concentrated in vacuo. The crude product is purified by silica gel chromatography to give 48 mg of the title compound as white foam. 1H NMR (CDCl3): 5.15 (br, 2H), 7.12-7.30 (m, 3H), 7.70 (d, J=8 Hz, 1H), 7.80-7.90 (m, 2H), 7.90-8.0 (dd, 1H), 8.5 (d, J=2 Hz, 1H). MS (m/z): 312 (M−1).

Workup

  1. additionis added
  2. filtrationfiltered through celite
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-a5b2a9e8c9f24f77b750b8d8e12052f6
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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