4-Methoxyphenol → 4-Bromomethyl-7-acetoxycoumarin

Participants

Reaction Steps

A quaternary ammonium salt of dimethylaminopropylmethacrylamide (DMAPMA) and 4-(bromomethyl)-7-acetoxycoumarin was synthesized in the following manner. One gram of 4-(bromomethyl)-7-acetoxycoumarin (available from TCI America; Portland, Oreg.), (3.36 mmol) was charged to a 100 mL round bottom flask equipped with a magnetic stir bar and a reflux condenser. Enough acetone (reagent grade or better) to dissolve the material at reflux was added (about 40 mL). N,N-Dimethylaminopropylmethacrylamide (DMAPMA, available from Rohm Tech. Inc.; Malden, Mass.), 1.43 g (2.5 equivalents) was dissolved in about 10 mL of acetone. 4-Methoxyphenol (available from Aldrich; Milwaukee, Wis.), 20 mg, was added to the DMAPMA/acetone solution, and this solution was added dropwise to the 4-(bromomethyl)-7-acetoxycoumarin using an addition funnel over the course of about 10 minutes. The reaction mixture was maintained at reflux for 2 hours, after which time the solution was allowed to cool to room temperature. Left to stand overnight, the product crystallized from the reaction mixture to form a fine white powder that was easily collected by filtration (1.53 g), and characterized by NMR.

Provenance & Evidence