Reaction #554642

Reaction equation

N-(1-(4-bromophenyl)propan-2-yl)acetamide

NaI

→

N-(1-(4-iodophenyl)propan-2-yl)acetamide

Solvents

dioxan

Conditions

Workup

1. 1
   Temperatureto cool to r.t.
2. 2
   Otherhalf of the solvent is removed in vacuo
3. 3
   workup.ADDITIONEtOAc and diluted aq. ammonia solution are added
4. 4
   Otherthe layers are separated
5. 5
   ExtractionThe aq. layer is once more extracted with EtOAc
6. 6
   Dryingdried with Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Otherthe solvent is removed in vacuo
9. 9
   OtherThe crude product is triturated with diethylether
10. 10
    Otherdried at 50° C. in vacuo

Procedure

To 6.00 g (23.4 mmol) N-(1-(4-bromophenyl)propan-2-yl)acetamide (II.1) in 65 mL dioxan are added 0.45 g (2.34 mmol) CuI, 0.50 mL (4.70 mmol) N,N″-dimethyl-ethylendiamine and 7.02 g (46.9 mmol) NaI. The reaction mixture is stirred at 120° C. for 70 h. The mixture is allowed to cool to r.t. and half of the solvent is removed in vacuo. EtOAc and diluted aq. ammonia solution are added and the layers are separated. The aq. layer is once more extracted with EtOAc. The organic layers are combined, dried with Na2SO4, filtered and the solvent is removed in vacuo. The crude product is triturated with diethylether and dried at 50° C. in vacuo.

Source