Triphenylphosphine → 10-Bromo-1-decene

Temperatur

0 °C

To a solution of dec-9-en-1-ol (1.22 g, 7.82 mmol) in DMF (18 mL) was added triphenylphosphine (2.30 g, 8.77 mmol). The solution was cooled to 0° C. and NBS (1.52 g, 8.54 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (0.8 mL). The solution was diluted with ether (80 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford 10-bromo-dec-1-ene (1.38 g, 81%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.80 (1H, m), 4.94 (2H, m), 3.38 (2H, t, J=6.9 Hz), 2.02 (2H, m), 1.83 (2H, m), 1.20–1.55 (10H, m); 13C NMR (75 MHz, CDCl3) δ 139.17, 114.30, 34.29, 34.02, 33.06, 29.53, 29.25, 29.12, 28.96, 28.40.

1. customthe reaction was quenched with methanol (0.8 mL)
2. additionThe solution was diluted with ether (80 mL)
3. washwashed with water, saturated aqueous NaHCO3 and brine successively
4. customThe organic layer was dried
5. concentrationconcentrated
6. customThe residue was purified by flash chromatography on silica gel
7. washeluting with hexane

ORD-Eintrag

ord-1e3ad5c77d6a4913a7de709d2d308fb0

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07091357B2