Phenethyl bromide → 3-Nitro-1-(2-phenylethyl)-1H-pyrazole

Participants

Reaction Steps

To a solution of 3-nitro-1H-pyrazole (226 mg, 2.0 mmol) in N,N-dimethylformamide (3 mL) were added potassium carbonate (0.33 g, 2.4 mmol) and 1-bromo-2-phenylethane (0.44 g, 2.4 mmol). The resulting mixture was stirred at rt overnight. TLC showed the reaction was complete. The mixture was diluted with EtOAc (40 mL), then washed with water (2×20 mL), brine (20 mL), and dried over anhydrous sodium sulfate. The crude material was purified by chromatography on silica gel, eluting with Hex:EtOAc=80:20→70:30 to give the title compound as a white solid. NOE experiment confirmed the structure. 1H NMR (CDCl3, 400 MHz): δ=3.22 (t, J=7.1 Hz, 2H), 4.43 (t, J=7.1 Hz, 2H), 6.79 (d, J=2.5 Hz, 1H), 7.06-7.09 (m, 2H), 7.12 (d, J=2.5 Hz, 1H), 7.23-7.32 (m, 3H).

Provenance & Evidence