Sodium hydride → 4-iodo-1-[(4-methoxyphenyl)methyl]-1H-pyrazole

Participants

Reaction Steps

To a stirred solution of 4-iodo-1H-pyrazole (1.50 g, 7.73 mmol) in dry DMF (15 mL) at 0° C. was added sodium hydride (9.28 mmol, 60% dispersion in mineral oil) and the reaction mixture was allowed to warm to room temperature. After the evolution of hydrogen had ceased, 4-methoxy-benzyl chloride (1.06 mL, 7.80 mmol) was added and the reaction was stirred for 2 h and then quenched with water (50 mL) and extracted with diethyl ether (100 mL). The organic layer was washed with water (3×30 mL) and brine, dried over magnesium sulphate and the solvent removed under vacuum. The crude residue was washed with small portions of hexane and dried in vacuo, providing the product as a white solid (2.26 g, 93% yield). 1H-NMR (CDCl3) δ 7.51 (s, 1H), 7.34 (s, 1H), 7.17 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.5 Hz, 2H), 5.21 (s, 2H), 3.78 (s, 3H).

Provenance & Evidence