Bromine → 2-bromo-1-(6-bromopyridin-3-yl)ethanone
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[Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:15]Br>C(Cl)(Cl)Cl.ClCCl>[Br:15][CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:10][Br:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:15]Br>C(Cl)(Cl)Cl.ClCCl>[Br:15][CH2:9][C:8]([C:5]1[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:10]1-(6-Bromopyridin-3-yl)ethanone was dissolved in 50 mL of chloroform and cooled to 0° C., to which was added catalytic amount of AlCl3 and 2.65 mL of bromine in 25 mL of chloroform. The addition of bromine lasted 1 h to keep the reaction solution at 0° C. After stirring at 0° C. overnight, the mixture was diluted with dichloromethane, washed with aqueous sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4), filtered, and concentrated to afford 2-bromo-1-(6-bromopyridin-3-yl)ethanone which was used in the next step with out further purification. LCMS: [M+1]+=279.
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