Potassium Phosphate, Tribasic → 4-Cyclopropyl-2-fluoro-3-trifluoromethylaniline

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-fluoro-3-trifluoromethylaniline (5.0 g, 19.4 mmol), cyclopropylboronic acid (2.16 g, 25.2 mmol), K3PO4 (14.4 g, 67.8 mmol) and tricyclohexyl phosphine (0.54 g, 1.9 mmol) are dissolved in toluene (80 mL) and water (4 mL). The solution is degassed with N2, heated to 90° C., and Pd(OAc)2 (0.22 g, 1.0 mmol) is added. The reaction is heated at 90° C. for 5 hours, cooled, diluted with Et2O, filtered, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue is purified by column chromatography (EtOAc/hexanes) to give 4-cyclopropyl-2-fluoro-3-trifluoromethylaniline.

Provenance & Evidence