Phenylboronic Acid → 1-Bromo-2-methyl-4-phenoxybenzene

Participants

Reaction Steps

Into a 100 mL round bottom flask was added 4-bromo-3-methylphenol (0.90 g, 0.0048 mol), phenylboronic acid (2.4 g, 0.019 mol), cupric acetate (1.4 g, 0.0077 mol) and DCM (49.99 mL). TEA (4.0 mL, 0.029 mol) was then added followed by 4 A° molecular sieves and the reaction mixture was stirred at rt over night. 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=2.35 (s, 3H), 6.72 (dd, J=8.59, 3.03 Hz, 1H), 6.91 (d, J=2.78 Hz, 1H), 6.98-7.05 (m, 2H), 7.08-7.16 (m, 1H), 7.31-7.38 (m, 2H), 7.46 (d, J=8.59 Hz, 1H).

Provenance & Evidence