Acetone → 4-Fluorobiphenyl

Participants

Reaction Conditions

Reaction Steps

To NaOH (480 mg, 12.0 mmol, 1.20 equiv) in MeOH (20 mL) at 23° C. was added 4-biphenylboronic acid (1.98 g, 10.0 mmol, 1.00 equiv). After stirring for 15 min at 23° C., the reaction mixture was cooled to 0° C. and was added to AgOTf (7.71 g, 30.0 mmol, 3.00 equiv). After stirring for 30 min at 0° C., the solvent was removed under reduced pressure at 0° C. and the residual MeOH was completely removed by co-evaporation with acetone (20 mL×2). To the residue was added acetone (50 mL), MS3 Å (5.0 g), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(trifluoroborate) (1) (3.72 g, 10.5 mmol, 1.05 equiv) and the reaction mixture was stirred for 30 min and concentrated in vacuo. The residue was dissolved in CH2Cl2 and filtered through a plug of Celite. After the removal of CH2Cl2, to the residue was added H2O (30 mL) and Et2O (30 mL) and the phases were separated. The aqueous phase was extracted with Et2O (2×20 mL). The combined organic phases are washed with brine (30 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes to afford 1.62 g of 4-fluorobiphenyl as a colorless solid (94% yield).

Provenance & Evidence