Potassium Phosphate, Tribasic → 5-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-pyrazole

Participants

Reaction Steps

A 75-mL pressure vessel was charged with 1-bromo-2-iodo-4-(trifluoromethyl)benzene (2.015 g, 5.74 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Aldrich, St. Louis, Mo., 1.374 g, 6.60 mmol), potassium phosphate (2.438 g, 11.48 mmol), and PdCl2(dppf)-CH2Cl2 adduct (Strem Chemicals Inc., Newburyport, Mass., 0.469 g, 0.574 mmol). The vessel was flushed with Ar (g), then DMF (19.14 ml) was added. The vial was sealed and placed in an 80° C. oil bath for 2 hours. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on an 80 g silica gel column to give 5-(2-bromo-5-(trifluoromethyl)phenyl)-1-methyl-1H-pyrazole (1.001 g, 3.28 mmol) as a yellow solid. [M+H]+=307.0.

Provenance & Evidence