Nitrobenzene → HCID 54354718, compound

Participants

Reaction Steps

4-Bromoveratrole (8.8 g, 40 mmol), indole-2-carboxylic acid ethyl ester (1.9 g, 10 mmol), potassium carbonate (1.9 g), copper- (I) bromide (o.2 g), pyridine (2 ml) and nitrobenzene (10 ml) were stirred at 140° C. for 14 hours. After cooling to room temperature, the reaction mixture was applied onto a silica gel flash chromatography column (silica gel: 140 g). The column was subsequently eluted with toluene (500 ml), toluene/acetone (95:5, 500 ml) and toluene/acetone (90:10, 500 ml). 1-(3,4-Dimethoxyphenyl)indole-2-carboxylic acid ethyl ester was eluted with toluene/acetone (90:10) and gave colorless crystals upon evaporation of the solvent. The crystals were triturated with diisopropyl ether, collected by vacuum filtration and dried in the air. Yield: 3.0 g. (92% of theoretical yield) M.pt.: 126°-128° C. Rf (toluene/acetone, 9:1)=0.53.

Provenance & Evidence