Reaktion #607056

Reaktionsgleichung

4-bromo-3-methylbenzylalcohol

2-cyanophenylboric acid

dichloromethane

sodium carbonate

→

title compound

Ausbeute 24.5%

4′-(hydroxymethyl)-2′-methylbiphenyl-2-carbonitrile

Ausbeute 24.5%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed under an argon atmosphere for 30 hr
2. 2
   EinengenThe reaction mixture was concentrated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   WaschenThe obtained ethyl acetate solution was washed with saturated brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   SonstigeThe solvent was evaporated under reduced pressure
7. 7
   Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

A mixture of 4-bromo-3-methylbenzylalcohol (15.16 g), 2-cyanophenylboric acid (14.80 g), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), dichloromethane adduct (3.08 g), tetrabutylammonium bromide (1.22 g), 2M aqueous sodium carbonate solution (75 mL) and toluene (300 mL) was refluxed under an argon atmosphere for 30 hr. The reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. The obtained ethyl acetate solution was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow oil (4.12 g, 24%).

Quelle