2-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamide → 2-(3,4-Dichlorophenyl)-1-phenylethanone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](N(OC)C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Under N2, to a mixture of 2-(3,4-dichlorophenyl)-N-methoxy-N-methylacetamide (440 mg, 1.8 mmol) in anhydrous THF was added phenylmagnesium bromide (4.4 mL, 4.4 mmol) at −78° C., and the mixture was stirred for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, washed with water and brine, concentrated, and purified by column chromatography (PE:EtOAc=20:1) to give Intermediate 6 (400 mg, yield 85%).