Ethyl Acetate → 5-Bromo-2-fluoro-3-phenylpyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-2-fluoropyridin-3-ylboronic acid (620 mg, 2.82 mmol) and 1-iodobenzene (292 μL, 2.6 mmol) in 1,4-dioxane (50 μL) was degassed via nitrogen bubble for 15 mins. Then the mixture was added Pd(PPh3)4 (150 mg, 0.13 mmol) and aqueous Na2CO3 (24 μL, 5.7 mmol) and heated to 90° C. for 30 mins. The reaction was cooled to room temperature and poured into ethyl acetate (50 mL). The mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated. The residue was purified via a flash column using 10% ethyl acetate in hexanes as an eluent. The product containing fractions were concentrated to give 5-bromo-2-fluoro-3-phenylpyridine (2.2) (326 mg, 49.8% yield).

Provenance & Evidence