Allyl bromide → HCID 57642378, compound

Participants

Reaction Steps

To a solution of 5.0 g (0.031 mole) of 5-chloro-3-methyl-4-nitro-1H-pyrazole in 100 mL of anhydrous tetrahydrofuran under argon, was added 0.37 g (0.0464 mole) of lithium hydride. The mixture was stirred at room temperature for 15 minutes. Then 5.6 g (0.0464 mole) of allyl bromide was added, and the mixture was heated at 80° C. for 10 hours. The mixture was cooled, poured onto ice and extracted twice with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexane (1:2) to give, as the more polar component, 1.36 g of 3-chloro-5-methyl-4-nitro-1-(2-propenyl)-1H-pyrazole as a colorless oil and, as the less polar component, 0.5 g of 5-chloro-3-methyl-4-nitro-1-(2-propenyl)-1H-pyrazole (XX) as a colorless oil.

Provenance & Evidence