Sodium Carbonate → 4-(3-Chloropyridin-2-yl)benzoic acid

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Reaction Steps

2,3-Dichloropyridine (2.66 g, 18.0 mmol), 4-carboxyphenylboronic acid (2.70 g, 16.3 mmol), and Pd(PPh3)4 (0.965 g, 0.835 mmol) were combined in a degassed solution of 1:1 0.5M aq Na2CO3:MeCN (120 mL), heated to 85° C. for 5 hours, filtered, and the filtrate concentrated under reduced pressure to remove most of the MeCN. The concentrate was extracted with CH2Cl2 (10 mL) and acidified with 1N HCl. The acidified solution was filtered and the filter cake dried under reduced pressure to provide the title compound as a solid.

Provenance & Evidence