[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])[CH:9]=1)[C:5]#[N:6].C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH2:18][Br:27])[C:12]=2[F:19])[CH:9]=1)[C:5]#[N:6]3-bromo-5-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (6.05 g, 17.76 mmol) and NBS (3.16 g, 17.76 mmol) were combined in carbon tetrachloride (100 mL) with a catalytic amount of AIBN (0.146 g, 0.888 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified on silica gel (eluted with 0 to 10% Et2O in hexanes) to give 3-bromo-5-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}benzonitrile (4.5 g, 10.73 mmol, 60.4% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92-7.95 (m, 1H), 7.52-7.61 (m, 4H), 4.75 (s, 2H).
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