Sodium Iodide → 1-((4-(2-Iodoethyl)phenoxy)methyl)benzene

Temperature

0 °C

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 AcOEt (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.

1. customto rise to room temperature
2. extractionThe reaction mixture is extracted with methylene chloride (2×300 ml)
3. washthe combined organic layers are then washed with brine (2×300 ml)
4. concentrationconcentrated under vacuum
5. stirringthe reaction mixture is stirred
6. temperatureunder reflux for 6 hours
7. filtrationAfter filtration
8. washthe organic layer is washed with brine (3×400 ml)
9. dry with materialdried with Na2SO4
10. filtrationfiltered
11. concentrationconcentrated under vacuum

ORD record

ord-e39b05db42544b7d8f75575d07c29983

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612238B2