Sodium Carbonate → 2-fluoro-4-(4-methoxyphenyl)benzonitrile

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Reaction Steps

A mixture of 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) was added to a solution of 4-bromo-2-fluorobenzonitrile (5.00 g, 25.0 mmol) and tetrakis(triphenylphosphine)palladium (578 mg, 0.50 mmol) in benzene (50 mL). The resulting mixture was treated with a 2.0 M aqueous solution of Na2CO3 (25 mL, 50 mmol) and heated briefly at reflux, then at 65° C. overnight. The mixture was cooled to room temperature and treated with 6.0 M aqueous NaOH. The aqueous phase was separated and extracted with ether. First the original organic phase and then the ethereal wash were filtered through diatomaceous earth. The collection flask was changed and the solids remaining atop the diatomaceous earth were washed through with EtOAc. The ethereal wash was concentrated and refiltered as before. The combined EtOAc rinses were combined and concentrated to provide the title compound as a yellow powder (92% yield). 1HNMR (300 MHz, d6-DMSO) δ 3.82 (s, 3H), 7.07 (d, 2H), 7.72 (dd, 1H), 7.79 (d, 2H), 7.85 (dd, 1H), 7.95 (dd, 1H).

Provenance & Evidence