Potassium Carbonate → 3-Fluoro-4-(6-hydroxynaphthalen-2-yl)benzoic acid

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6-Bromonaphthalen-2-ol (1 g, 4.48 mmol) was mixed with 880 mg of 2-fluoro-4-(methoxycarbonyl)phenylboronic acid (4.48 mmol), 1.2 g of K2CO3 (9.23 mmol), 120 mg of Pd(PPh3)4 (2.5 mol %), and then suspended in 17 mL of 1,4-Dioxane and 4 mL of H2O. The mixture was degassed 3× with argon and then heated to reflux while stirring for 1 hour. 4N NaOH (5 mL) was then added and stirred at room temperature for 2 hours, back extracted with EtOAc, and filtered through Celite. The basic aqueous solution was then acidified to pH=4.3 and the solids were filtered to give about 950 mg of off-white solid. This was triturated in 8 mL DCM and 2 mL EtOAc and filtered to yield about 830 mg of off-white Example 2 (65.8% overall yield). 1H-NMR (DMSO-d6 500 MHz): δ 13.31 (bs, 1H), 9.97 (bs, 1H), 8.05 (s, 1H), 7.90 (m, 2H), 7.80 (m, 3H), 7.64 (dt, 1H), 7.19 (m, 2H); MS (ESI): m/z 281.53 [MA]−.

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