3-Iodobenzoic acid → 3-Iodo-N-methoxy-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-Iodo-benzoic acid (5.0 g, 20.15 mmol), thionyl chloride (3.6 g, 30.2 mmol), and DMF (10 mL) in CH2Cl2 (100 mL) was heated to reflux for 3 h. The reaction was then concentrated under reduced pressure and the residue was dissolved in CH2Cl2 (100 mL). O,N-Dimethylhydroxylamine hydrochloide (2.16 g, 22.2 mmol) was added and the solution was cooled to 0° C. N,N-diisopropylethylamine (2.6 g, 20.2 mmol) was added drop wise. The reaction was warmed to room temperature. After 4 h the reaction was quenched with water, the layers were separated and the aqueous layer was extracted with CH2Cl2 (1×). The combined organic layers were dried over Na2SO4. Purification by flash column chromatography (hexanes/ethyl acetate 6:4) afforded the title compound as a white solid (3.69 g, 63%). MS: 291.8 (MH+); HPLC Rf: 4.87 min. (HPLC method 4).

Provenance & Evidence