Reaktion #48223

Reaktionsgleichung

Triphenylphosphine

3-(4-benzyloxy-phenylsulfanyl)-propan-1-ol

carbon tetrabromide

NaHCO3

→

1-Bromo-3-(4-benzyloxy-phenylsulfanyl)-propane

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was transferred into a separation funnel
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried over sodium sulphate ad
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (25 mL)
6. 6
   workup.ADDITIONhexane (100 mL) was added
7. 7
   workup.STIRRINGwith stirring
8. 8
   FiltrationThe precipitated triphenylphosphine oxide was filtered off
9. 9
   Waschenwashed with more EtOAc/hexane-mixture (1:4, 100 mL)
10. 10
    EinengenThe organic solutions were concentrated
11. 11
    Sonstigethe residue was purified by column chromatography (ethyl acetate/hexane, 1:10, Rf: 0.48)
12. 12
    Sonstigeafter a couple of days

Vorschrift

Triphenylphosphine (7.90 g, 30.0 mmol) was added to a solution of 3-(4-benzyloxy-phenylsulfanyl)-propan-1-ol (CAB02032, 4.12 g, 15.0 mmol) and carbon tetrabromide (4.98 g, 18.0 mmol) in dichloromethane (120 mL) at 0° C. (ice/water bath). The reaction mixture was allowed to warm up to room temperature and was stirred for another hour. The solution was transferred into a separation funnel and conc. NaHCO3-solution (50 mL) was added. The organic layer was separated, dried over sodium sulphate ad concentrated under reduced pressure. The residue was dissolved in ethyl acetate (25 mL) and hexane (100 mL) was added with stirring. The precipitated triphenylphosphine oxide was filtered off and washed with more EtOAc/hexane-mixture (1:4, 100 mL). The organic solutions were concentrated and the residue was purified by column chromatography (ethyl acetate/hexane, 1:10, Rf: 0.48). Yield: 4.96 g (98%) colourless oil, which becomes a solid after a couple of days. 1H-NMR (400 MHz, CDCl3) δ=2.07 (tt, i=7.0, 7.0 Hz, 2H, 2.95 (t, J=7.0 Hz, 2H), 3.50 (t, J=7.0 Hz, 2H), 5.04 (s, 2H, —OCH2Ph), 6.92 (d, J=9.0 Hz, 2H), 7.27-7.44 (m, 7H). 13C-NMR (100.5 MHz, CDCl3) 6=32.30, 32.50, 34.41, 70.44, 115.84, 126.15, 127.72, 128.31, 128.86, 133.65, 136.89, 158.43.

Quelle