Phenylboronic Acid → 1-Bromo-4-phenoxy-2-(trifluoromethoxy)benzene

Participants

Reaction Steps

4-Bromo-3-(trifluoromethoxy)phenol (1.0 g, 0.0039 mol), phenylboronic acid (1900 mg, 0.016 mol), TEA (3.2 mL, 0.023 mol), cupric acetate (1.3 g, 0.0070 mol) and DCM (40 mL) were added to a 100 mL oven dried flask and the reaction was stirred at rt for 48 h. Reaction mixture was then filtered through celite. The filtrate was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 5% EtOAc in hexane. 1H NMR (400 MHz, CDCl3): δ=6.82 (dd, J 8.97, 2.65 Hz, 1H), 7.00 (dd, J=2.78, 1.26 Hz, 1H), 7.02-7.10 (m, 2H), 7.16-7.24 (m, 1H), 7.36-7.45 (m, 2H), 7.55 (d, J=8.84 Hz, 1H).

Provenance & Evidence