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

HRID 873616Notes

Reaction equation

HRID 873616 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-4956454624f640a1b9a582fbc5f02c74
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

Loading…