Pyridine → 2,2'-Dimethylbiphenyl

Participants

Reaction Steps

To a nitrogen purged three-neck 100 mL flask was added nickel(II) bromide (0.22 grams, 1 mmole), polyvinyl pyridine (0.63 grams of Reillex® 402 obtained from Reilly Tar and Chemical Company, Indianapolis, IN), triphenylphosphine (2.62 grams, 10 mmole), 2-chlorotoluene (2.53 grams 20 mmole) and tetrahydrofuran (20 mL). The mixture was stirred at room temperature for 5 minutes and then tertiary-butyl-magnesium chloride (12 mL of 2.0 Molar solution in THF, 24 mmole) was added dropwise over a 10 minute period. The reaction warmed upon addition and at the end of the addition was heated to reflux for 14 hours. The mixture was cooled to ambient and analyzed by conventional gas chromatographic methods. The results of the reaction are:

Provenance & Evidence