Reaction #577248

Reaction equation

sodium iodide

2-(4-benzyloxy-phenyl)-ethanol

triethylamine

mesylchloride

→

1-Benzyloxy-4-(2-iodo-ethyl)-benzene

Solvents

ethyl acetate

methylene chloride

Conditions

Workup

1. 1
   Otherto rise to room temperature
2. 2
   ExtractionThe reaction mixture is extracted with methylene chloride (2×300 ml)
3. 3
   Washthe combined organic layers are then washed with brine (2×300 ml)
4. 4
   Concentrationconcentrated under vacuum
5. 5
   workup.STIRRINGthe reaction mixture is stirred
6. 6
   Temperatureunder reflux for 6 hours
7. 7
   FiltrationAfter filtration
8. 8
   Washthe organic layer is washed with brine (3×400 ml)
9. 9
   Dryingdried with Na2SO4
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated under vacuum

Procedure

To a solution of 2-(4-benzyloxy-phenyl)-ethanol (78.72 g, 0.34 mol) in methylene chloride (400 ml) is added triethylamine (67.3 ml, 0.44 mol, 1.4 eq), then at 0° C. is added mesylchloride (34.8 ml, 0.44 mol, 1.3 eq). The reaction mixture is stirred at 0° C. for 30 minutes and allowed to rise to room temperature. The reaction mixture is extracted with methylene chloride (2×300 ml), the combined organic layers are then washed with brine (2×300 ml) and concentrated under vacuum. To the crude product in solution in ethyl acetate (600 ml) is added sodium iodide (67.2 g, 0.44 mol, 1.3 eq) and the reaction mixture is stirred under reflux for 6 hours. After filtration, the organic layer is washed with brine (3×400 ml), dried with Na2SO4, filtered and concentrated under vacuum. 1-Benzyloxy-4-(2-iodo-ethyl)-benzene is isolated after crystallization with diethyl ether (116.5 g, 86%).

Source