Hydrogen Bromide → HCID 12845802, compound

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Reaction Steps

Thus, 3-butenyltrimethylsilane, prepared from trimethylchlorosilane and the Grignard reagent of 4-bromo-1-butene, undergoes the free radical catalyzed addition of hydrogen bromide to give 4-bromobutyltrimethylsilane. The reaction of an alkyl bromide with sodium nitrite in dimethylsulfoxide gives a nitroalkane with alkyl nitrites as byproducts. This reaction proceeds smoothly with 4-bromobutyltrimethylsilane to give 4-nitrobutyltrimethylsilane. The oxidative nitration reaction of this compound gave 4,4-dinitrobutyltrimethylsilane, which, under standard aqueous fluorination conditions, gave 4-fluoro-4,4-dinitrobutyltrimethylsilane. The reaction sequence may be summarized by the following equations: ##STR2##

Provenance & Evidence