Potassium Carbonate → 3-Bromo-5-{6-[2-(2-ethoxycarbonyl-ethyl)-3-(3-ethoxycarbonyl-propoxy)-phenyl]-hexyloxy}-benzoic Acid tert-butyl Ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (9.48 g, 20.1 mmol), 3-bromo-5-hydroxy-benzoic acid tert-butyl ester (5.0 g, 18.3 mmol) in N,N-dimethylformamide (100 mL) and acetone (200 mL) was added potassium carbonate (25.3 g, 183 mmol) at room temperature. The resulting suspension was heated to 70° C. for 24 h. Then, the reaction mixture was cooled to room temperature and diluted with water and 10% aq. HCl. The organic compound was extracted into ethyl acetate and the combined organic extracts were washed with water and brine solution. The organic layers were dried over anhydrous sodium sulfate and removal of the solvent under reduced pressure gave the crude product which was purified on a silica gel column eluting with 0-20% ethyl acetate in hexanes to afford the title compound (12 g, 99%) as a colorless oil.

Provenance & Evidence