Reaction #81760

Reaction equation

2-Ethyl-bromohexane

triiodophenol

potassium carbonate

2-(2,4,6-triiodophenoxy)butane

→

2-ethyl-1-(2,4,6-triiodophenoxy)-hexane

Yield 73.7%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Temperaturethe reaction was cooled
2. 2
   Filtrationfiltered through a pad of celite
3. 3
   Otherevaporated in vacuo
4. 4
   Washwashed with water (200 ml), 1N aqueous sodium hydroxide (200 ml), water (2×200 ml) and brine (200 ml)
5. 5
   Dryingdried (Na2SO4)
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated

Procedure

2-Ethyl-bromohexane (10.4 g, 53.0 mmol), triiodophenol (25.5 g, 54.0 mmol) and potassium carbonate (7.5 g, 54.3 mmol) were reacted in dry DMF (110 ml) at 77° C as for 2-(2,4,6-triiodophenoxy)butane. After stirring for 20 hrs, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up in EtOAc (500 ml), washed with water (200 ml), 1N aqueous sodium hydroxide (200 ml), water (2×200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated. Flash column chromatography (silica, hexanes) provided 2-ethyl-1-(2,4,6-triiodophenoxy)-hexane (22.8 g, 73.7%) as a clear viscous oil.

Source