Br[CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[C:12]([Cl:20])=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[N-:22]=[N+:23]=[N-:24].[Na+].O>CS(C)=O>[N:22]([CH2:2][C:3]1[C:4]([F:21])=[C:5]([O:10][C:11]2[C:12]([Cl:20])=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1)=[N+:23]=[N-:24]3-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile (0.65 g, 1.587 mmol) and sodium azide (0.114 g, 1.746 mmol) were combined in DMSO (7 mL) and stirred overnight at 25° C. Water was added to the reaction mixture to give a white precipitate. The reaction mixture was stirred for 15 min at room temperature, filtered, washed with water, and air dried to give 3-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile (0.565 g, 1.521 mmol, 96% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.02 (d, J=2.20 Hz, 1H), 7.50-7.63 (m, 2H), 7.31 (d, J=1.74 Hz, 1H), 4.61 (s, 2H).
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