Vinyltrimethylsilane → 4-Bromo-2-ethoxy-1-vinylbenzene

HRID 735664Notes

Reaction equation

HRID 735664 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:14]([O:19]CC)[CH:13]=1.C[Si](C)(C)C=C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([O:19][CH2:14][CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 79102VinyltrimethylsilaneHCID 225986564-Bromo-2-methyl-1-vinylbenzene2×HCID 509981894-Bromo-2-ethoxy-1-iodobenzene

Product 1

HCID 578428364-Bromo-2-ethoxy-1-vinylbenzeneYield 88%

Procedure

Using a procedure analogous to that used to prepare 30A, 62C (2 g, 6.1 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 62D (1.4 g, 88%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.44 (t, J=7.03 Hz, 3 H) 4.02 (q, J=6.74 Hz, 2 H) 5.27 (d, J=10.99 Hz, 1 H) 5.74 (d, 1 H) 6.92-7.01 (m, 2 H) 7.04 (d, 1 H) 7.31 (d, J=7.91 Hz, 1 H).

Sources & evidence

ORD record
ord-911746136a804eb7bd4963c9a993ce8b
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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