Reaktion #2486374

Reaktionsgleichung

ethanol

2,5-dibromopyrimidine

3-benzyloxybenzeneboronic acid

sodium carbonate

→

5-bromo-2-(3-benzyloxyphenyl)pyrimidine

Ausbeute 70.3%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is subsequently partitioned between ether and water
2. 2
   Waschenthe organic phase is washed twice with sodium chloride solution
3. 3
   Trocknendried over sodium sulfate
4. 4
   Sonstigeevaporated
5. 5
   Sonstigethe residue is purified by chromatography (silica gel/dichloromethane)

Vorschrift

15.00 g (63.10 mmol) of 2,5-dibromopyrimidine (for preparation see: D. W. Arantz and D. J. Brown in Journal of the Chemical Society C, 1971, p. 1889), 14.40 g (63.10 mmol) of 3-benzyloxybenzeneboronic acid, 13.40 g (126.2 mmol) of sodium carbonate and 0.73 g (0.63 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 4 hours in 150 ml of toluene, 75 ml of ethanol and 50 ml of water. The reaction mixture is subsequently partitioned between ether and water, the organic phase is washed twice with sodium chloride solution, dried over sodium sulfate and evaporated, and the residue is purified by chromatography (silica gel/dichloromethane), giving 15.14 g of 5-bromo-2-(3-benzyloxyphenyl)pyrimidine. ##STR14##

Quelle