Reaktion #69982

Reaktionsgleichung

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

sodium tert-butoxide

1-bromo-4-iodobenzene

4-(piperidin-4-yloxy)pyridine

→

4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine

Ausbeute 50.9%

Lösungsmittel

Ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenthe mixture is washed twice with water and once with a saturated aqueous sodium chloride solution
2. 2
   TrocknenThe organic phase is dried over magnesium sulphate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe crude product obtained
5. 5
   Sonstigeis chromatographed on silica gel, elution

Vorschrift

2 g of 1-bromo-4-iodobenzene and 1.386 g of 4-(piperidin-4-yloxy)pyridine are placed in 35 ml of toluene and then 0.324 g of tris(dibenzylideneacetone)dipalladium(0), 0.245 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 1.019 g of sodium tert-butoxide are added. The reaction medium is heated at 110° C. for 18 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 gradient of a dichloromethane/methanol (99/1 to 98/2) mixture. 1.2 g of 4-[1-(4-bromophenyl)piperidin-4-yloxy]pyridine are obtained.

Quelle