Sodium Carbonate → 4-(6-(Trifluoromethyl)pyridin-3-yl)phenol

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-(trifluoromethyl)pyridine (1.18 g, 5.51 mmol), 4-hydroxyphenylboronic acid (775 mg, 5.51 mmol) and sodium carbonate (2.34 g, 22.0 mmol) were combined and dissolved in a mixture of dioxane/water (30 mL/6 mL). The reaction mixture was degassed and then tetrakistriphenylphosphinepalladium (0) (322 mg, 0.275 mmol) was added and the reaction mixture was heated at 70° C. for 18 hours. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified on silica gel by Biotage™ (7% to 60% EtOAc in heptane over 20 CV) to give the title compound (1.24 g, 95%) as a white solid.

Provenance & Evidence