Potassium Carbonate → HCID 21936374, compound

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of 4-(trifluoromethyl)phenylboronic acid (5.05 g, 26.59 mmol) in dioxane/water (15/15 mL) is added 4-bromo-2-fluoro-benzaldehyde (4.91 g, 24.17 mmol), tetrabutylammonium bromide (7.79 g, 24.17 mmol, potassium carbonate (9.18 g, 66.48 mmol) and is degassed for 10 min. Palladium(II) acetate (895 mg, 1.33 mmol) is added and the reaction mixture is heated to 70° C. After 2 h TLC (20% EtOAc/hexane) indicates complete consumption of starting material. The reaction is cooled to room temperature diluted with water and extracted with EtOAc (3×200 mL). The combined organic extracts are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (330 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (5.57 g, 86%). 1NMR (400 MHz, CDCl3) δ ppm: 10.41 (s, 1H), 7.98 (t, 1H, J=7.5 Hz), 7.74 (q, 4H, J=7.8 Hz), 7.52 (d, 1H, J=7.9 Hz), 7.41 (dd, 1H, J=11.2, 1.2 Hz).

Provenance & Evidence