4-Bromophenol → 4-(4-Trifluoromethylphenyl)phenol

Participants

Reaction Steps

4-(trifluoromethyl)phenylboronic acid (263 mg, 1.39 mmol) was suspended in water (2 mL). 4-bromophenol (0.200 g, 1.16 mmol), potassium carbonate (484 mg, 3.47 mmol), and palladium(II) acetate (13.3 mg, 0.0580 mmol) were added. The reaction was allowed to stir open to ambient atmosphere for 60 hours. The reaction was filtered through Celite and extracted three times with ethyl acetate. The combined organics were washed with 1N HCl, water, and brine, dried over magnesium sulfate, filtered and concentrated. Purification by column chromatography (0-20% ethyl acetate in heptanes) gave 4′-(trifluoromethyl) biphenyl-4-ol (150 mg, 55%) as a white solid. 1H NMR (400 MHz, CDCl3, δ): 7.63-7.70 (m, 4H), 7.50-7.54 (m, 2H), 6.95 (d, J=8.8 Hz, 2H), 4.81 (s, 1H). MS (M−1): 237.0.

Provenance & Evidence