Tridecane → 4-Methoxybiphenyl

Participants

Reaction Conditions

Reaction Steps

A slurry of magnesium bromide (0.74 g; 4.0 mmol) in THF (3 mL) was treated at room temperature with phenyllithium (2.4 mL of 1.7 M solution; 4.0 mmol). The solution was heated at 60° C. for 30 min, and was then treated at 60° with lithium t-butoxide (4.4 mL of 1.0 M solution in THF; 4.4 mmol) and heating was continued for 1 h. The reaction solution was cooled to room temperature and treated with a solution of 4-methoxybenzonitrile (0.27 g, 2.0 mmol), dichlorobis(trimethylphosphine)nickel (0.028 g; 5 mol %), and tridecane (0.18 g; 1.0 mmol; internal GC standard) in THF (2 mL). The reaction was then heated to 60° and stirred for 2 h. A sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and ether. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 1.67 mmol (84% yield) of 4-phenylanisole, 0.18 mmol of 4-methoxybenzophenone imine, and no remaining 4-methoxybenzonitrile in the reaction mixture.

Provenance & Evidence