Reaction #44761

Reaction equation

1-(2-chloroethoxy)-4-(benzyl)benzene

sodium iodide

water

→

1-(2-iodoethoxy)-4-(benzyl)benzene

Yield 72.9%

Solvents

2-butanone

Conditions

Workup

1. 1
   Temperatureat reflux for 16 hours
2. 2
   TemperatureAfter cooling
3. 3
   ExtractionThe mixture was extracted with ethyl acetate
4. 4
   WashThe organic layer was washed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure

Procedure

A solution of 1-(2-chloroethoxy)-4-(benzyl)benzene (734 mg, 2.97 mmol) and sodium iodide (1.78 g, 11.9 mmol) in 2-butanone (30 mL) was heated at reflux for 16 hours. After cooling, water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure. Flash chromatography gave 732 mg of 1-(2-iodoethoxy)-4-(benzyl)benzene, 1H NMR (300 MHz, CDCl3) δ 7.29 (dd, 2H), 7.19 (dd, 1H), 7.18 (d, 2H), 7.11 (d, 2H), 6.84 (d, 2H), 4.23 (t, 2H), 3.94 (s, 2H), 3.41 (t, 2H) ppm.

Source