4-chloro-N-methoxy-N-methyl-3-(methylsulfonyl)benzamide → 1-(4-Chloro-3-(methylsulfonyl)phenyl)ethanone
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
Product 1
Reagents, catalysts & solvents 1
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.