Isopropyltriphenylphosphonium iodide → 1-Bromo-12-methyl-11-tridecene

Temperature

-40 °C

Isopropyltriphenylphosphonium iodide (6 g, 14 mmoles) was suspended in tetrahydrofuran (120 ml), stirred at -40° C. and treated with n-butyllithium (14 mmoles) dissolved in hexane (2.5M). The mixture was stirred at -40° C. for 15 minutes, cooled to -75° C. and treated with a solution of 1-bromo-11-oxoundecane (2.8 g, 11.5 mmoles) in tetrahydrofuran (30 ml). The mixture was stirred at -75° C. for 15 minutes, allowed to warm to 25° C. and concentrated in vacuo. The residue was triturated with hexane, filtered and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel eluted with hexane to afford 1-bromo-12-methyl-11-tridecene.

1. stirringThe mixture was stirred at -40° C. for 15 minutes
2. temperaturecooled to -75° C.
3. stirringThe mixture was stirred at -75° C. for 15 minutes
4. temperatureto warm to 25° C.
5. concentrationconcentrated in vacuo
6. customThe residue was triturated with hexane
7. filtrationfiltered
8. concentrationthe filtrate concentrated in vacuo
9. customThe residue was chromatographed on silica gel
10. washeluted with hexane

ORD record

ord-52ad35343bd5454ca3aa594c0b1b0640

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04769386