Dimethylformamide → HCID 57586569, compound

Participants

Reaction Steps

To a mixture of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (14.54 g, 30.84 mmol), 3,5-dibromophenol (8.55 g, 33.92 mmol), and potassium carbonate (8.53 g, 61.68 mmol) were added N,N-dimethylformamide (210 mL) and acetone (420 mL) at room temperature. The resulting suspension was heated to reflux for 2 days. Then, the reaction mixture was cooled to room temperature and diluted with water (200 mL). The organic compound was extracted into ethyl acetate (2×200 mL) and the combined organic extracts were washed with brine solution (200 mL). The organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give the crude product which was purified by using a Biotage column chromatography (FLASH 40L, Silica), eluting with 10% ethyl acetate/hexanes to obtain 4-{3-[6-(3,5-dibromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (19.61 g, 99%) as a colorless oil: ES(+)-HRMS m/e calculated for C29H38O6Br2 (M+H)+ 641.1108, found 641.1101.

Provenance & Evidence