Hydrogen Bromide → HCID 12845802, compound

HRID 1390525Notes

Reaction equation

[CH2:1]([Si:5]([CH3:8])([CH3:7])[CH3:6])[CH2:2][CH:3]=[CH2:4].C[Si](C)(C)Cl.[Br:14]CCC=C.Br>>[Br:14][CH2:4][CH2:3][CH2:2][CH2:1][Si:5]([CH3:8])([CH3:7])[CH3:6]

Participants

Reactant 4

HCID 260Hydrogen Bromide

HCID 6397Chlorotrimethylsilane

HCID 21241Homoallyl bromide

HCID 262843but-3-enyl(trimethyl)silane

Product 1

HCID 12845802HCID 12845802, compound

Procedure

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##

Sources & evidence

ORD record: ord-9fdd6c157cc24fd29214f06f5774d0cc
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139403

Reaction notes

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