Acetic Anhydride → 6-Chloro-8-iodocoumarin

Participants

Reaction Steps

A mixture of 3-iodo-5-chlorosalicylaldehyde (100 g, 0.354 mole), acetic anhydride (300 mL) and triethylamine (54 mL) was heated at reflux for 18 hours. Upon cooling, the desired coumarin precipitated as a dark brown crystalline material. The precipitate was filtered, washed with hexane/ethyl acetate (4:1, 200 mL), and air dried. [Yield: 60 g (55% yield)]. Additional quantities of the desired product (10 g, 9% yield) can be obtained from the filtrate, upon storage.

Provenance & Evidence