Sodium Carbonate → HCID 57586574, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-dibromophenol (500 mg, 1.98 mmol) in dimethoxyethane (12.5 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, the solid tetrakis(triphenylphosphine)palladium(0) (496 mg, 0.43 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this period, a solution of 1,4-benzodioxane-6-boronic acid (536 mg, 2.98 mmol) in ethanol (12.5 mL) was added followed by a solution of sodium carbonate (421 mg, 3.97 mmol) in water (0.5 mL). The resulting light yellow suspension was stirred for 4 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (20 mL) and ethyl acetate (30 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo gave the colored residue which was purified by using an ISCO 120 column, eluting with 10-30% ethyl acetate in hexanes to afford 3,5-bis-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenol (386 mg, 54%) as an amorphous light brown solid: ES(+)-HRMS m/e calculated for C22H18O5 (M+H)+ 363.1227, found 363.1226.

Provenance & Evidence