Cesium fluoride → HCID 66718285, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 1 Step 2, 8.0 g, 30.8 mmol), 2-(trifluoromethyl)phenylboronic acid (8.8 g, 46.3 mmol), cesium fluoride (14.0 g, 92.4 mmol), palladium acetate (0.69 g, 3.1 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxybiphenyl (3.16 g, 7.7 mmol) was prepared in a mixture of dioxane (80 mL) and water (80 mL) under nitrogen atmosphere and heated at 100° C. for 12 hours. The reaction mixture was concentrated under vacuum. The residue was diluted with EtOAc (200 mL), and then washed with water (100 mL) and brine (100 mL). The organic layer was dried (Na2SO4) and concentrated under vacuum. After purification by flash chromatography (silica, pet ether/EtOAc), the title compound was obtained as a pale yellow solid (8.0 g, 88%). 1H NMR (CDCl3, 400 MHz) δ 8.22 (1H, s), 7.99 (1H, d, J=6.5 Hz), 7.78 (1H, d, J=7.7 Hz), 7.57 (2H, m), 7.27 (2H, m), 4.19-4.10 (2H, m), 3.95 (3H, s), 3.26 (3H, s).

Provenance & Evidence