Reaktion #9881

Reaktionsgleichung

NBS

trans-oct-3-en-1-ol

triphenylphosphine

→

trans-1-bromo-oct-3-ene

Ausbeute 73.3%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction was quenched with methanol (1 mL)
2. 2
   workup.ADDITIONThe solution was diluted with ether (100 mL)
3. 3
   Waschenwashed with water, saturated aqueous NaHCO3 and brine successively
4. 4
   SonstigeThe organic layer was dried
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash chromatography on silica gel
7. 7
   Wascheneluting with hexane

Vorschrift

To a solution of trans-oct-3-en-1-ol (1.28 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.1 mmol). The solution was cooled to 0° C. and NBS (1.92 g, 10.8 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 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 trans-1-bromo-oct-3-ene (1.40 g, 73%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 5.54 (1H, m), 5.39 (1H, m), 3.37 (2H, t, J=7.2 Hz), 2.54 (2H, m), 2.02 (2H, m) 1.34 (4H, m), 0.89 (3H, t, J=7.2 Hz); 13C NMR (75 MHz, CDCl3) δ 134.09, 126.45, 36.34, 33.21, 32.48, 31.73, 22.45, 14.24.

Quelle