Réaction #69978

Équation de réaction

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

sodium tert-butoxide

1-bromo-4-iodobenzene

1,4-dioxa-8-azaspiro[4.5]decane

→

8-(4-bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

Rendement 58.8%

Solvants

Ethyl acetate

toluene

Conditions de réaction

Traitement

1. 1
   Températureto reflux of the solvent for 4 h
2. 2
   Lavagethe mixture is washed twice with water and once with a saturated aqueous sodium chloride solution
3. 3
   SéchageThe organic phase is dried over magnesium sulphate
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   AutreThe crude product obtained
6. 6
   Autreis chromatographed on silica gel, elution

Mode opératoire

0.5 g of 1-bromo-4-iodobenzene and 0.3 g of 1,4-dioxa-8-azaspiro[4.5]decane are placed in 10 ml of toluene and then 0.08 g of tris(dibenzylideneacetone)dipalladium(0), 0.061 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 0.255 g of sodium tert-butoxide are added. The reaction medium is brought to reflux of the solvent for 4 h. Ethyl acetate is subsequently added and the mixture is washed twice with water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a heptane/ethyl acetate (4/1) solvent mixture. 0.31 g of 8-(4-bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane is obtained.

Source