[NH2:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)C>[NH2:1][C:2]1[C:13]([F:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:5]To a solution of 2-amino-5-chloro-3-fluoro-N-methoxy-N-methyl-benzamide (250 mg, 1.07 mmol) in diethyl ether (5 ml) was added phenylmagnesium bromide (2.69 ml, 1M in THF, 2.69 mmol) dropwise at 0° C. The resulting mixture was stirred for 2.5 h at 0° C. and the quenched by addition of saturated NH4Cl solution. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 98:2-95:5) to afford the title compound (189 mg, 70%) as yellow solid. MS (ESI): 250.2 (M+H)+.
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