[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[C:12]#[N:13])=[C:6]([F:21])[C:5]([CH3:22])=[CH:4][CH:3]=1.[Br:23]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:22][C:5]1[C:6]([F:21])=[C:7]([O:8][C:9]2[CH:10]=[C:11]([CH:14]=[C:15]([C:17]([F:18])([F:19])[F:20])[CH:16]=2)[C:12]#[N:13])[C:2]([Cl:1])=[CH:3][CH:4]=1To a solution of 3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-5-(trifluoromethyl)benzonitrile (12.2 g, 37.0 mmol) and N-bromosuccinimide (6.59 g, 37.0 mmol) in carbon tetrachloride (300 mL) was added AIBN (0.304 g, 1.850 mmol) and the mixture was stirred at 75° C. for 4 hours. More AIBN (0.304 g, 1.850 mmol) was added and the reaction mixture was stirred overnight at 75° C. The mixture was filtered through a pad of Celite and the filtrate was concentrated. The crude oil was purified via silica gel chromatography to give 3-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-5-(trifluoromethyl)benzonitrile (7.33 g, 17.94 mmol, 49% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.63 (s, 1H), 7.42 (s, 1H), 7.31-7.36 (m, 2H), 7.24 (d, 1H), 4.48 (s, 2H).
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