Dimethylformamide → HCID 18399427, compound

Participants

Reaction Steps

To a solution of 2-(3,5-dibromo-4-methoxybenzoyl)-4,5-dimethoxy-benzoic acid (6.30 g) in dimethylformamide (50 ml) are added potassium carbonate (4.04 g) and dimethyl bromomalonate (3.43 g), and the mixture is stirred at room temperature overnight. To the reaction mixture are added ethyl acetate and water. The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. To the residue are added dioxane (30 ml) and conc. hydrochloric acid (30 ml), and the mixture is heated under reflux for five hours. The reaction mixture is cooled, and thereto are added ethyl acetate and water. The ethyl acetate layer is separated, and washed. The remaining aqueous layer is acidified with 10% hydrochloric acid, and then extracted with ethyl acetate. The extract is washed, and dried. The extracts are combined, and concentrated under reduced pressure. The residue is crystallized from ether to give 4(3,5-dibromo-4-methoxyphenyl)-6,7-diethoxy-isocoumarin-3-carboxylic acid (1.32 g) as listed in Table 58.

Provenance & Evidence