1,1-Dibromoethane → 1-Trityl-4-(4-cyanobenzyl)5-methylimidazole

Participants

Reaction Conditions

Reaction Steps

To a suspension of activated zinc dust (0.262 g, 3.99 mmol) in THF (1 mL) was added dibromoethane (0.035 mL, 0.039 mmol) and the reaction stirred under argon at 20° C. for 45 minutes. The suspension was cooled to 0° C. and a-bromo-p-tolunitrile (0.51 g, 2.60 mmol) in THF (3 mL) was added dropwise over a period of 10 minutes. The reaction was then allowed to stir at 20° C. for 45 minutes and bis(triphenylphosphine)Nickel II chloride (0.130 g, 0.399 mmol) and 5-iodo-1-trityl imidazole (15.95 g, 36.6 mmol) were added in one portion The resulting mixture was stirred 3 hours at 20° C. and then quenched by addition of saturated NH3 solution (2 mL) and the mixture stirred for 3 hours, extracted with EtOAc (2×25 mL), dried (MgSO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 20% EtOAc in CH2Cl2 to afford the title compound as a white solid.

Provenance & Evidence