Cesium carbonate → HCID 57586468, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,5-dibromophenol (59.54 mmol, 15 g), 3,4-(methylenedioxy) phenylboronic acid (77.40 mmol, 12.84 g), 3-thiopheneboronic acid (62.52 mmol, 8 g), PdCl2(dppf) (6.75 mmol, 4.94 g), and cesium carbonate (240 mmol, 78.19 g) was added dimethoxyethane (550 mL) at room temperature under nitrogen atmosphere. Then, the resulting light brown suspension was heated to 97° C. and stirred for 15 h. Then, the reaction mixture was cooled to room temperature and the solids were filtered-off and the cake was washed with ethyl acetate. The filtrate was diluted with water (300 mL) and the two layers were separated. The aqueous layer was extracted with ethyl acetate (2×100 mL) and the combined organic extracts were washed with brine solution (300 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent gave the crude dark brown residue which was purified by two times using an ISCO (330 g) column chromatography eluting with 0-20% ethyl acetate in hexanes to afford the desired 3-benzo[1,3]dioxol-5-yl-5-thiophen-3-yl-phenol (7.48 g, 42.5%) as a white low melting solid. HRES(+) m/e calcd for C17H12O3S (M+H)+ 297.0580, found 297.0580

Provenance & Evidence