Azobisisobutyronitrile → 8-Bromo-2-(bromomethyl)quinoline

Participants

Reaction Steps

To a solution of 2 (2.5477 g, 11.47 mmol) in carbon tetrachloride (40 mL) was added NBS (2.2461 g, 12.62 mmol) and a little bit of AIBN followed by refluxing overnight under UV light. The mixture was filtered to remove the solid and concentrated to give a yellow solid. Purification by chromatography (hexanes/DCM 80:20) yielded a white solid.(1.33 g, 39%) 1H NMR (400 MHz CDCl3) δ8.16 (1H, d, J=8.4 Hz), 8.05 (1H, d, J=7.2 Hz), 7.78 (1H, d, J=7.6 Hz), 7.65 (1H, d, J=8.4 Hz), 7.41 (1H, t, J=7.6 Hz), 4.78 (3H, s); 13C NMR (300 MHz CDCl3) δ158.3, 144.7, 138.0, 133.9, 128.9, 127.7, 127.6, 125.1, 122.4, 34.6; EIMS, m/z 299/300/301 (M/M+1/M+2).

Provenance & Evidence