4-chloro-N-methoxy-N-methyl-3-(methylsulfonyl)benzamide → 1-(4-Chloro-3-(methylsulfonyl)phenyl)ethanone

HRID 1845143Notes

Reaction equation

HRID 1845143 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15].[CH3:18][Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH3:18])=[CH:4][C:3]=1[S:14]([CH3:17])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 581073914-chloro-N-methoxy-N-methyl-3-(methylsulfonyl)benzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 581882281-(4-Chloro-3-(methylsulfonyl)phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A round bottom flask was charged with 4-chloro-N-methoxy-N-methyl-3-(methylsulfonyl)benzamide (18.0 g, 64.9 mmol) and tetrahydrofuran (200 mL) at 0° C. Methylmagnesiumbromide (1M solution in THF, 78 mL, 78 mmol) was added slowly and the reaction was stirred for 3 h at that temperature. The reaction was then quenched with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were concentrated under reduced pressure and the residue was purified by flash chromatography to get the title compound.

Workup

  1. customThe reaction was then quenched with aqueous ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layers were concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e187ae654982486094a513dcbf0ac83c
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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