Potassium Carbonate → HCID 86687643, compound

Participants

Reaction Steps

A round-bottom flask was charged with 1-bromo-4-iodo-2-methoxybenzene (Combi-Blocks, Inc., San Diego, Calif., 6.25 g, 19.97 mmol), (3,5-difluorophenyl)boronic acid (3.47 g, 21.97 mmol), potassium carbonate (8.28 g, 59.9 mmol), and PdCl2(dppf)-CH2Cl2 (0.816 g, 0.999 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (30.0 ml) and water (9.99 ml) were added in sequence. The mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was taken up in DCM and loaded onto a pre-equilibrated 340-g SNAP Ultra column. The column was eluted with 0-10% EtOAc/Heptane containing 5% DCM. Fractions containing the desired product were combined and concentrated. The residue was taken up in heptane and filtered. The collected solid was washed with heptane (3×), then dried under a stream of N2 (g). The process was repeated with the filtrate to give a second crop of material. The two crops were dried under vacuum to give 4-bromo-3′,5′-difluoro-3-methoxy-1,1′-biphenyl as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=7.66 (d, J=8.2 Hz, 1H), 7.58-7.49 (m, 2H), 7.40 (d, J=1.9 Hz, 1H), 7.33-7.20 (m, 2H), 3.96 (s, 3H). m/z (ESI) 301.1.

Provenance & Evidence