Toluene → 4-Iodo-N-methoxy-N-methyl-benzamide

Participants

Reaction Conditions

Reaction Steps

N,O-Dimethylhydroxylamine hydrochloride (5.5 g, 56.4 mmol) was added to a suspension of 4-iodobenzoyl chloride (10.0 g, 37.5 mmol) and toluene (60 mL) at 0° C. After 10 min, a solution of sodium carbonate (16.0 g, 151 mmol) and water (250 mL) was added over 50 min via addition funnel. With vigorous stirring, the reaction was maintained at 0° C. for 2 h and then partitioned. The toluene layer was washed with water (125 mL), washed with brine (125 mL), and then concentrated. The residue was redissolved in toluene and filtered to remove trace solids. This solution was concentrated to give 10.5 g of 4-iodo-N-methoxy-N-methylbenzamide as a colorless oil. 1H NMR (400 MHz, DMSO-d6): δ 7.83 (d, 2H), 7.32 (d, 2H), 3.53 (s, 3H), 3.25 (s, 3H); LCMS: 292.4 (M+H)+. Step 2: 1-(4-Iodophenyl)-2-(4-methoxyphenyl)ethanone

Provenance & Evidence