Reaktion #2486375

Reaktionsgleichung

ethanol

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

4-octyloxybenzeneboronic acid

sodiumcarbonate

→

2-(3-benzyloxyphenyl)-5-(4-octyloxyphenyl)pyrimidine

Ausbeute 97.6%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture is subsequently partitioned between water and ether
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: ethyl acetate=98:2)

Vorschrift

8.00 g (23.40 mmol) of 5-bromo-2-(3-benzyloxyphenyl)pyrimidine, 7.03 g (28.10 mmol) of 4-octyloxybenzeneboronic acid (preparation analogous to 3-benzyloxybenzeneboronic acid), 7.00 g (65.52 mmol) of sodiumcarbonate and 0.27 g (0.23 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 2 hours in 200 ml of toluene, 100 ml of ethanol and 50 ml of water. The reaction mixture is subsequently partitioned between water and ether, 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: ethyl acetate=98:2), giving 10.66 g of 2-(3-benzyloxyphenyl)-5-(4-octyloxyphenyl)pyrimidine. ##STR15## 10.66 g (22.84 mmol) of 2-(3-benzyloxyphenyl)-5-(4-octyloxyphenyl)pyrimidine are hydrogenated together with 2.00 g of Pd (10%)/C in 100 ml of tetrahydrofuran until the calculated volume of hydrogen has been consumed, the catalyst is subsequently filtered off, and the filtrate is evaporated and dried, giving 8.43 g of 2-(3-hydroxyphenyl)-5-(4-octyloxyphenyl)pyrimidine.

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