Methyl iodide → HCID 15516432, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-diiodo-4-(4′-methoxyphenoxy)benzyl alcohol (9) (347 mg; 0.72 mmol) in dry THF under argon was cooled to 0° C. and treated with 60% sodium hydride in mineral oil (28 mg; 0.7 mmol). The reaction was stirred at 0° C. for 10 min, then allowed to warm to RT and stirred an additional 30 min. Methyl iodide (0.5 ml; 8.1 mmol) was added and the mixture stirred at RT for 18 h. The reaction was poured into saturated NH4Cl (20 ml) and extracted with EtOAc (20 ml). The organic layer was washed with saturated NaCl, dried over Drierite, and evaporated to a tan oil which solidified upon standing. The solid was dissolved in a minimum amount of CH2Cl2 (3 ml), applied to a silica gel column (30 g, 230-400 mesh) and eluted with EtOAc/hexanes (3:17). Product-containing fractions were combined and evaporated to give 231 mg of 3,5-diiodo-4-(4′-methoxyphenoxy)benzyl methyl ether (10) as a white solid. NMR (CDCl3) d 3.41 (s, 3H), 3.76 (s, 3H), 6.70 (m, 2H), 6.81 (m, 2H), 7.80 (s, 2H). TLC: Rf0.69 (EtOAc/hexanes, 3:7)

Provenance & Evidence