Potassium Phosphate, Tribasic → Perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with perfluorophenyl 5-bromonaphthalene-2-sulfonate (285.84 mg, 0.631 mmol), (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid (277 mg, 1.261 mmol), potassium phosphate (402 mg, 1.892 mmol), and Pd(AmPhos)2Cl2 (22.33 mg, 0.032 mmol). The vial was flushed with Ar (g), then dioxane (1577 μl) and water (526 μl) was added. The vial was sealed and heated in a microwave for 20 min at 90° C. The mixture was diluted with water and extracted with EtOAc (three times). The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The product was purified by chromatography on silica gel (0 to 20% EtOAc/Heptane) to give perfluorophenyl 5-(2-methoxy-4-(trifluoromethyl)phenyl)naphthalene-2-sulfonate (228.1 mg, 0.416 mmol) as a white foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.62 (d, J=1.9 Hz, 1H), 8.07 (d, J=8.2 Hz, 1H), 7.85 (dd, J=2.0, 9.0 Hz, 1H), 7.79-7.71 (m, 2H), 7.64 (dd, J=1.3, 7.1 Hz, 1H), 7.47-7.38 (m, 2H), 7.29 (s, 1H), 3.77 (s, 3H).

Provenance & Evidence