Triphenylphosphine → HCID 15781018, compound

Participants

Reaction Conditions

Reaction Steps

2-bromo-4-fluorophenol (4.16 g, 20.32 mmol, Aldrich) was added into the flask, and then nitrogen was introduced thereto. Palladium acetate (0.22 g, 1.02 mmol), potassium phosphate (21.00 g, 91.19 mmol), phenylboronic acid (2.97 g, 24.36 mmol) and triphenylphosphine (0.80 g, 3.06 mmol) were additionally added into the flask. DME (32 ml) and distilled water (8 ml) were added into, followed by stirring well. The mixture was heated to 50° C. and then stirred for 6 hours. After completion of the reaction, the reaction product was cooled to room temperature, and the organic layer was separated with ammonium chloride diethylether (10 ml×3) and distilled water. Then, magnesium sulfate was added to the collected organic layer, followed by stirring for 30 minutes. The mixture was filtered and treated to remove volatile material, thus obtained material was cooled to −78° C. followed by slowly adding borontribromide (30.48 ml, 1.0M in methylene chloride Aldrich) dropwise. After completion of the addition, the mixture was maintained at that temperature for 1 hour, and then warmed to room temperature and stirred for 12 hours. Then, the organic layer was separated with ammonium chloride diethylether (10 ml×3) and distilled water from the obtained material. Subsequently, magnesium sulfate was added to the collected organic layer, followed by stirring for 30 minutes. After filtering, removing volatile components, and the residue was passed through a silica gel chromatography column using a mixed solvent of hexane and methylene chloride (1.5:1) as moving phase. From obtained mixture, volatile components were removed to yield 3.76 g of 2-phenyl-4-fluorophenol as white solid.

Provenance & Evidence