Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CN(C=O)C>[CH3:11][C:4]1[CH:3]=[CH:2][C:7]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]To a DMF solution (5.0 ml) of 4-bromo-2-methyl-1-nitro-benzene (500 mg), palladium acetate (10.4 mg), S-Phos (38.0 mg) and potassium phosphate (983 mg), phenylboronic acid-pinacol ester (496 mg) was added, and then the mixture was degassed under ultrasonic irradiation. After the mixture was stirred at 100° C. for 18 hours, water (20 ml) was added, followed by extraction with ethyl acetate (20 ml×2), and the organic layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the solvent was distilled off under reduced pressure, followed by purification by silica gel column chromatography (hexane/ethyl acetate=100/1), to obtain the desired compound (457 mg, 93%).
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