Potassium Carbonate → HCID 23004900, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-hydroxy acetophenone (1.00 g, 4.65 mmol), 4-(trifluoromethyl)phenylboronic acid (1.32 g, 6.97 mmol), potassium carbonate (1.30 g, 9.38 mmol), tetrakis(triphenylphosphine)palladium (0) (538 mg, 0.465 mmol) in 1,4-dioxane (30.0 mL) and water (18.0 mL) was heated to 60° C. for 18 hours under nitrogen. The reaction was allowed to cool to room temperature and concentrated in vacuo to afford a dark brown oil which was dissolved in ethyl acetate (50 mL) and filtered through Arbocel™. The Arbocel™ was washed with ethyl acetate (100 mL). The combined organics were washed sequentially with a 0.5M aqueous solution of hydrogen chloride (2×50 mL) and brine (2×100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a brown oil (2.12 g). The oil was then purified by silica gel column chromatography (5%-10% ethyl acetate in heptane gradient elution) to afford the title compound as a yellow solid (795 mg, 61%).

Provenance & Evidence