4-(Bromomethyl)benzoic acid → HCID 43627730, compound

Participants

Reaction Steps

To a solution of 4-(bromomethyl)benzoic acid (10.7 g) in chloroform (200 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (10.5 g), 1-hydroxybenzotriazole monohydrate (8.38 g), N,O-dimethylhydroxylamine hydrochloride (4.85 g), and triethylamine (6.94 mL) were added. After stirring the mixture at room temperature for 53 hours, chloroform (200 mL) was added. The mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate, a saturated aqueous solution of ammonium chloride, and saturated brine successively. After passage through a phase separator, the washed mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-40:60) to give 4-(chloromethyl)-N-methoxy-N-methylbenzamide as a colorless oil (3.23 g).

Provenance & Evidence