Hydrogen Bromide → Bromide ion

HRID 1390526Notes

Reaction equation

[Br:1][CH2:2][CH2:3][CH:4]=[CH2:5].[CH3:6][Si:7]([CH3:10])([CH3:9])Cl.C([Si](C)(C)C)CC=C.[BrH:19]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][Si:7]([CH3:10])([CH3:9])[CH3:6].[Br-:19]

Participants

Reactant 4

HCID 260Hydrogen Bromide

HCID 6397Chlorotrimethylsilane

HCID 21241Homoallyl bromide

HCID 262843but-3-enyl(trimethyl)silane

Product 2

HCID 259Bromide ionYield 90%

HCID 12845802HCID 12845802, compound

Procedure

4-Bromobutyltrimethylsilane was prepared by the procedure of Perklev, Chem. Abstr., 49, 1541 (1955), involving the preparation of the Grignard reagent from 4-bromo-1-butene, its reaction with trimethylchlorosilane to give 3-butenyltrimethylsilane, and free radical catalyzed HBr addition. The latter addition gave 90% primary bromide. Using inadequate initiator gave mainly secondary bromide.

Workup

customto give
additionThe latter addition

Sources & evidence

ORD record: ord-017ed1266c90497a950d9c95ea10d3d7
Source dataset: uspto-grants-1979_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04139403

Reaction notes

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