Methyl iodide → N-(3-fluorophenyl)-3-iodo-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.11 g of 60% NaH in mineral oil) was added to a solution of CH3I (4.53 g) and N-(3-fluorophenyl)-3-iodobenzamide (7.26 g) in DMF (120 mL) at 0° C. under nitrogen. After being stirred at 0° C. for another 5 minutes, the reaction was stirred at room temperature under nitrogen for 4 h. The reaction was quenched by slow addition of saturated aqueous NH4Cl (120 mL), followed by addition of water (100 mL). The mixture was extracted with diethyl ether (300 mL×2). The combined ether layers were washed by water (150 mL×4) and brine (150 mL×1), dried by Na2SO4 and concentrated to give crude product (7.56 g), which was purified by column chromatography to afford N-(3-fluoro-phenyl)-3-iodo-N-methylbenzamide (5.88 g; 78%). 1H NMR (600 MHz, DMSO-d6) δ 7.64 (m, 2H), 7.28 (m, 1H), 7.24 (d, 1H, J=7.5 Hz), 7.19 (m, 1H), 7.04-6.99 (m, 3.33 (s, 3H).

Provenance & Evidence