2-Chlorobenzonitrile → 2-Cyano-4'-methylbiphenyl

Participants

Reaction Steps

7.65 mg of Pd2 (dba)3 (8.35 μmol) and 11.60 mg of Ligand 2 (33.33μmol) were combined in 5 ml of solvent (dioxane, toluene, or 2-propanone) and stirred at room temperature for 2 hours to form a catalyst solution that was used in this example and other examples. CsF (2.28 g, 15.0 mmol), 2-chlorobenzonitrile (0.689 g, 5.00 mmol), and p-tolueneboronic acid (0.748 g, 5.50 mmol) were taken up in 14 ml of dry dioxane under nitrogen and a 0.1 mol % aliquot from the catalyst solution (in dioxane) was added. The mixture was then heated to 80° C. for 12 hours. The mixture was then cooled to room temperature, diluted with Et2O, and extracted with a saturated NH4Cl solution (3×20 ml). The Et2O layer was dried over MgSO4, filtered and concentrated to give a viscous oil which was purified by flash chromatography to give 844 mg of 2-cyano-4'-methylbiphenyl in 87% isolated yield.

Provenance & Evidence