Sodium hydride → HCID 59240049, compound

Participants

Reaction Steps

At 0° C. NaH (60%, 400 mg, 10 mmol) was added to a stirred mixture of 1-(2,6-dichlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-ol (1.5 g, 5 mmol) and 4-bromobenzyl bromide (1.5 g, 6 mmol) in dry DMF (20 mL), the resulting mixture was stirred at ambient temperature for 1 h, then quenched with aqueous NH4Cl at 0° C., extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by column chromatography (30% EtOAc/hexanes) to give 5-(4-bromobenzyloxy)-1-(2,6-dichlorophenyl)-3-trifluoromethyl-1H-pyrazole as a white solid (2.2 g, 94%). 1H-NMR (CDCl3): δ 7.47-7.41 (m, 4H), 7.36-7.33 (m, 1H), 7.17 (d, 2H), 5.93 (s, 1H), 5.08 (s, 2H), MS (ESI): 467[M+H]+.

Provenance & Evidence