4-Iodo-N-methoxy-N-methyl-benzamide → 1-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

4-Iodo-N-methoxy-N-methylbenzamide (3.4 g, 11.7 mmol) was added dropwise over 5 min (internal temperature kept below 5° C.) to a vigorously stirring solution of (4-methoxybenzyl)magnesium chloride (52 mL, 0.25M in 2-MeTHF, 13 mmol) at 0° C. under N2. After 10 min, a white precipitate was observed. After 5 hours of vigorous stirring at 0° C., the reaction was quenched with 1N HCl (50 mL). When the internal temperature returned to 0° C., the reaction was filtered, and the filter cake was washed with ethyl acetate (50 mL) (Note #1). The filter cake was dried under vacuum to give 2.7 g of 1-(4-iodophenyl)-2-(4-methoxyphenyl)ethanone as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.92 (d, 2H), 7.78 (d, 2H), 7.16 (d, 2H), 6.87 (d, 2H), 4.28 (s, 2H), 3.72 (s, 3H).

Provenance & Evidence