Tridecane → 4-Methoxybiphenyl

Participants

Reaction Steps

A solution of zinc chloride (0.48 g; 3.5 mmol) in THF (5 mL) was treated at 0° C. with phenylmagnesium chloride (2.1 mL of a 1.40 M solution in THF; 3.0 mmol) and then stirred at room temperature for 30 min. The mixture of phenylzinc chloride thus obtained was then 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mol %), and tridecane (0.18 g; 1.0 mmol; internal GC standard) in THF (2 mL) and heated at 60° C. for 8 h. A sample was withdrawn and quenched in a mixture of 1 M sodium citrate (aq) and ether.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 0.90 mmol (45% yield) of 4-phenylanisole, no 4-methoxybenzophenone imine, 0.38 mmol of anisole, 0.82 mmol of biphenyl, 0.23 mmol of 4,4′-dimethoxybiphenyl, and 0.09 mmol of 4-methoxybenzonitrile remaining in the reaction mixture.

Provenance & Evidence