Iodine → p-Iodocumene

Participants

Reaction Conditions

Reaction Steps

(C9H11I), FW=246.09 g/mol. Cumene (45.0 g, 377 mmol), iodine (38.25 g, 151 mmol) and iodic acid (15.38 g, 87.4 mmol) were dissolved in a solution of acetic acid (188 mL), water (30 mL), dichloromethane (19 mL), and sulfuric acid (7.5 mL). The solution was heated to 85° C. for three hours. Once the reaction was complete, the reaction was worked up with water and dichloromethane. The dichloromethane was washed with sodium hydrosulfite, dried over magnesium sulfate and concentrated, yielding a red liquid in 94% yield. Rf 0.63 (hexanes) 1H NMR (300 MHz, CDCl3, ppm) d 7.58 (d, 2H, J=8.3 Hz), 6.96 (s, 2H, J=8.3 Hz), 2.83 (septet, 1H, J=6.9 Hz), 1.20 (d, 6H, J=6.9 Hz); 13C NMR (75.5 MHz, CDCl3, ppm) d 148.2, 137.2, 128.5, 90.7, 33.6, 23.8; LR MS (EI) m/z 246.

Provenance & Evidence