p-Bromoacetophenone → 1-Bromo-4-(prop-1-en-2-yl)benzene

To a solution of triphenylphosphonium bromide (17.94 g, 50.24 mmol) in DMSO (10 ml) was added n-BuLi (39.25 ml, 1.6M solution in hexane, 62.80 mmol). The solution was stirred at rt for 1 h and to this was added a solution of 4-bromoacetophenone (10.00 g, 50.24 mmol) in DMSO (4 ml). The reaction mixture was then stirred at rt overnight and then quenched with water and the product was extracted with pentane. The organic layers were combined washed with brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by filtration through a short pad of silica using pentane as eluant to give 1-bromo-4-isopropenylbenzene (5.23 g, 53%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.45 (d, J=9.0 Hz, 2H), 7.32 (d, J=9.0 Hz, 2H), 5.36 (m, 1H), 5.10 (m, 1H), 2.12 (m, 3H).

1. stirringThe reaction mixture was then stirred at rt overnight
2. customquenched with water
3. extractionthe product was extracted with pentane
4. washThe organic layers were combined washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a residue which
9. filtrationwas purified by filtration through a short pad of silica

ORD-Eintrag

ord-79570d942cfa40f5aed0615cfbfef6d1

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07259183B2