Iodine → 1-Fluoro-4-iodo-2-isopropyl-5-methoxybenzene

Participants

Reaction Steps

A solution of the 2-fluoro-1-isopropenyl-4-methoxybenzene (Example 76, 1.96 g, 11.81 mmol) in MeOH (30 ml) was charged with hydrogen at 1 atm with catalytic amount of Pd/C. The mixture was stirred at room temperature for 1 h. The mixture was filtered through Celite. The filtrate was then added to a mixture of silver sulfate (3.68 g, 11.81 mmol) and Iodine (3.00 g, 11.81 mmol) in MeOH (10 ml). The mixture was stirred at room temperature for 3 h until the color of solution became light yellow. The mixture was filtered and the filtrate was concentrated. The title compound was obtained after flash column using EtOAc:hexane 5:95 as the elute. 1H NMR (CDCl3, 500 MHz) δ 7.61 (d, J=8.0 Hz, 1H), 6.56 (d, J=12.5 Hz, 1H), 3.90 (s, 3H), 3.18 (m, 1H), 1.28 (m, 6H).

Provenance & Evidence