Reaktion #70917

Reaktionsgleichung

4-benzyloxy-3-methoxyphenylboronic acid

2-(3-bromophenyl)-6-(trifluoromethyl)pyridine

sodium carbonate

→

2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine

Lösungsmittel

toluene

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to room temperature
2. 2
   SonstigeThe phases were separated
3. 3
   Extraktionthe aqueous phase was extracted with toluene (5 mL)
4. 4
   WaschenThe combined organic phases were washed with water and brine
5. 5
   Trocknendried over anhydrous sodium sulphate
6. 6
   Filtrationfiltered
7. 7
   SonstigeEvaporation of the solvent
8. 8
   workup.WAITleft a brown oil that
9. 9
   Sonstigewas chromatographed over silica gel (petroleum ether/ethyl acetate, 9:1)

Vorschrift

To a stirred solution of 4-benzyloxy-3-methoxyphenylboronic acid (1.0 g, 3.87 mmol) and 2-(3-bromophenyl)-6-(trifluoromethyl)pyridine (1.063 g, 3.52 mmol) in toluene (10 mL) and ethanol (1 mL) at room temperature under argon was added 2 N aqueous sodium carbonate solution (5.41 mL, 10.82 mmol) followed by tetrakis(triphenylphosphine)palladium (0.22 g, 0.19 mmol). The resulting mixture was stirred at 90° C. for two hours and then allowed to cool to room temperature. The phases were separated and the aqueous phase was extracted with toluene (5 mL). The combined organic phases were washed with water and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent left a brown oil that was chromatographed over silica gel (petroleum ether/ethyl acetate, 9:1) to give 2-(4′-(benzyloxy)-3′-methoxybiphenyl-3-yl)-6-(trifluoromethyl)pyridine as a clear oil, 1.072 g (70%).

Quelle