Cesium carbonate → 6-Chloro-4'-fluorobiphenyl-3-ol

Participants

Reaction Conditions

Reaction Steps

A solution of 4-fluorophenylboronic acid (500 mg, 3.57 mmol), 4-chloro-3-iodophenol (455 mg, 1.79 mmol) and caesium carbonate (1.75 g) in dioxane (10 mL) and water (5 mL) was degassed 1 hour with nitrogen. Tetrakis(triphenylphosphine)palladium (0) (104 mg, 0.09 mmol) was added and the reaction mixture was heated for 18 hours at 75° C. The cooled reaction mixture was concentrated in vacuo and the residual aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic layer were dried over MgSO4, filtered and evaporated. The residue was purified by silica gel chromatography eluting with 20% ethyl acetate in heptane to afford the title compound (280 mg, 70%) as a yellow oil.

Provenance & Evidence