Phenylboronic Acid → HCID 58442404, compound

Participants

Reaction Steps

To a solution of 4-acetyl-3,5-dimethylphenyl trifluoromethanesulfonate (1.00 g, 3.38 mmol), KF (0.65 g, 11 mmol), and phenylboronic acid (0.49 g, 4.0 mmol) in THF (4.0 mL) was added tricyclohexylphosphine (11.4 mg, 0.04 mmol) and Pd(OAc)2 (7.6 mg, 0.03 mmol). The reaction mixture was stirred at room temperature for 5.0 h under N2. The reaction mixture was filtered through a small pad of Celite, and the cake was washed with ethyl acetate (40 mL). The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography on silica gel to give 1-(3,5-dimethyl-[1,1′-biphenyl]-4-yl)ethanone (0.68 g) in 90% yield: 1H NMR (500 MHz, CDCl3) δ 7.56 (d, J=8.0 Hz, 2 H), 7.44 (t, J=7.0 Hz, 2 H), 7.35 (m, 1 H), 7.25 (s, 2 H), 2.52 (s, 3 H), 2.33 (s, 6 H).

Provenance & Evidence