Vinyltrimethylsilane → 4-Bromo-2-chloro-1-ethenylbenzene

HRID 735656

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4](C)[CH:3]=1.BrC1C=CC(I)=C([Cl:19])C=1.C[Si](C)(C)C=C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([Cl:19])[CH:3]=1

Participants

Reactant 3

HCID 79102Vinyltrimethylsilane

HCID 27355474-Bromo-2-chloro-1-iodobenzene

HCID 225986564-Bromo-2-methyl-1-vinylbenzene2×

Product 1

HCID 578427134-Bromo-2-chloro-1-ethenylbenzeneYield 96%

Procedure

Using a procedure analogous to that used to prepare 30A, 4-bromo-2-chloro-1-iodobenzene (8 g, 25 mmol) was reacted with trimethyl(vinyl)silane in a pressure vessel at 160° C. for 1 h and worked up in a manner similar as in 30A to yield 61A (5.2 g, 96%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 5.41 (d, J=11.86 Hz, 1 H) 7.02 (dd, J=17.36, 11.21 Hz, 1 H) 7.35 (dd, 1 H) 7.41 (d, 1 H) 7.52 (d, J=1.76 Hz, 1 H).

Sources & evidence

ORD record: ord-2d460e143a7a461f97b4fc39ac894499
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592331B2

Linked notes

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