Reaction #48223

Reaction equation

Triphenylphosphine

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

carbon tetrabromide

NaHCO3

→

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

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherThe solution was transferred into a separation funnel
2. 2
   OtherThe organic layer was separated
3. 3
   Dryingdried over sodium sulphate ad
4. 4
   Concentrationconcentrated 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
   Washwashed with more EtOAc/hexane-mixture (1:4, 100 mL)
10. 10
    ConcentrationThe organic solutions were concentrated
11. 11
    Otherthe residue was purified by column chromatography (ethyl acetate/hexane, 1:10, Rf: 0.48)
12. 12
    Otherafter a couple of days

Procedure

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.

Source