Triphenylphosphine → 1-Bromooct-3-yne

Temperature

0 °C

To a solution of oct-3-yn-1-ol (1.26 g, 10.0 mmol) in DMF (25 mL) was added triphenylphosphine (2.92 g, 11.2 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 (150 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 1-bromo-oct-3-yne (1.35 g, 71%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.40 (2H, d, J=7.2 Hz), 2.78 (2H, m), 2.15 (2H, m), 1.22 (4H, m), 0.88 (3H, t, J=6.9 Hz); 13C NMR (75 MHz, CDCl3) δ 82.83, 77.05, 31.18, 30.63, 23.68, 22.20, 18.67, 13.89.

1. customthe reaction was quenched with methanol (1 mL)
2. additionThe solution was diluted with ether (150 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 record

ord-d45dd811ad1242be89b10cf1539f2c95

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091357B2