Potassium Phosphate, Tribasic → 2,2,2-Trifluoroethyl 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 2,2,2-trifluoroethyl 5-bromonaphthalene-2-sulfonate (0.211 g, 0.572 mmol), (4-chloro-2-methoxyphenyl)boronic acid (0.128 g, 0.687 mmol), potassium phosphate (0.486 g, 2.289 mmol), and Pd(dppf)Cl2 CH2Cl2 (0.047 g, 0.057 mmol). The vial was sealed with a septum cap and flushed with N2. Dioxane (2.60 mL) and water (0.260 mL) were added and the mixture was sparged with N2 for 1 minute, then heated at 84° C. for 2 h. The resulting mixture was filtered through diatomaceous Earth® (diatomaceous earth) and concentrated to a residue for purification by MPLC. The residue was taken up in minimal CH2Cl2 and absorbed onto a 5 g loading cartridge and passed through a silica gel column (12 g) using a 98:2 Heptane:EtOAc to 100% EtOAc gradient to afford 2,2,2-trifluoroethyl 5-(4-chloro-2-methoxyphenyl)naphthalene-2-sulfonate (0.176 g, 0.409 mmol) as a colorless amorphous solid.

Provenance & Evidence