Azobisisobutyronitrile → 4-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile

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To a solution of 4-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-3-fluorobenzonitrile (2.41 g, 8.62 mmol) and NBS (1.534 g, 8.62 mmol) in carbon tetrachloride (150 ml) was added AIBN (1.415 g, 8.62 mmol) and the reaction mixture was stirred at 80° C. overnight. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile (1.60 g, 4.46 mmol, 52% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (dd, 1H), 7.62 (d, 1H), 7.48-7.59 (m, 2H), 6.92 (t, 1H), 4.70 (s, 2H).

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