Sodium Carbonate → (2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

After toluene (150 ml), ethanol (30 ml) and distilled water (30 ml) were added to 4-(cyanomethyl)-2-ethylphenyl trifluoromethanesulfonate (9.7 g, 33 mmol) obtained in Example (26-2), 4-methoxyphenylboronic acid (5.3 g, 35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (2.7 g, 3.3 mol) and sodium carbonate (10.0 g, 94 mmol), the mixture was stirred at 80° C. for 4 hours. After the reaction mixture was cooled to room temperature, the insolubles were removed by filtration. The obtained filtrate was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=7/1-6/1) to give (2-ethyl-4′-methoxy-1,1′-biphenyl-4-yl)acetonitrile as an oil (5.5 g, yield: 66%).

Provenance & Evidence