Azobisisobutyronitrile → 3-(6-Bromo-3-bromomethyl-2-fluoro-phenoxy)-5-chloro-benzonitrile

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Reaction Conditions

Reaction Steps

A mixture of 3-[(6-bromo-2-fluoro-3-methylphenyl)oxy]-5-chlorobenzonitrile (8.1 g, 23.78 mmol), NBS (5.08 g, 28.5 mmol) and AIBN (0.195 g, 1.189 mmol) in CCl4 (240 ml) was heated at 90° C. for 16 h under an atmosphere of nitrogen. The mixture was cooled to 0° C., filtered thru Celite and concentrated. The crude yellow oil was purified on silica gel (hexanes/ethyl acetate) to give 2.75 g (26%) of 3-{[6-bromo-3-(bromomethyl)-2-fluorophenyl]oxy}-5-chlorobenzonitrile as a clear oil. 1H NMR (400 MHz, chloroform-d) δ ppm 7.44 (dd, 1H), 7.34 (t, 1H), 7.18-7.32 (m, 1H), 7.13 (t, 1H), 6.89-7.05 (m, 1H), 4.45 (d, 2H).

Provenance & Evidence