Hexachloroethane → 1-Ethyl-4-nitro-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-1-ethyl-4-nitro-1H pyrazole (1 equiv) in THF (0.6 M) was added dropwise a 1.0 M solution of lithium bis(trimethylsilyl)amide (2.6 equiv) at −78° C. The reaction mixture was stirred at −78° C. for 30 min before the addition of hexachloroethane (1.5 equiv) in THF (1.2 M). The mixture was stirred at −78° C. for 2.5 h then warmed to room temperature. The reaction was diluted with brine (1.8 M) and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (10-15% ethyl acetate in petroleum ether) to afford the desired product as a white solid (88.2% yield). MS (ESI) m/z 176.0 [M+H]+.

Provenance & Evidence