Bromine → 4-bromo-3-tert-butyl-1-(2-methoxy-6-methylphenyl)-1H-pyrazol-5-amine

Participants

Reaction Steps

To a solution of 3-tert-butyl-1-(2-methoxy-6-methylphenyl)-1H-pyrazol-5-amine (2.00 g, 7.71 mmol) (Intermediate C) in acetic acid (15 mL) was added bromine (1170 mg, 0.38 mL, 7.33 mmol) dropwise. The reaction mixture was stirred for 5 min at rt, and then diluted with water (100 mL), causing a solid to precipitate. The solid was collected by filtration, then dissolved in EtOAc. The organic phase was then washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to afford product (2683 mg, 102%) containing minor impurities. ES-MS m/z 338.2 (MH+); HPLC RT (min) 3.06.

Provenance & Evidence