1,2-Dibromoethane → 1-Trityl-4-(4-cyanobenzyl)imidazole

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Reaction Steps

To an oven dried 500 ml flask was added Zn (92 mmol, 5.96 g) and then 45 mL of distilled THF via syringe. To this well stirred mixture was added 1,2-dibromoethane (9.2 mmol, 1.72 g) via pipet. This mixture was stirred at ambient temperature for 3 hr and then a solution of p-cyanobenzylbromide (59.5 mmol, 11.68 g) in THF (50 mL) was added via addition funnel over 20 minutes. The resulting mixture was stirred at ambient temperature for 6 hr. Then a mixture of 1-trityl-4-iodoimidazole (45.8 mmol, 20 g) and bis-triphenylphosphinedichloronickel (4.6 mmol, 3.0 g) was added. This was stirred at ambient temperature for 36 hr. A saturated ammonium chloride solution (125 mL) was added. Stirring was continued for 3 hr and then 1 L of chloroform was added to this mixture. The chloroform layer was drawn off, washed with dilute sodium bicarbonate then saturated sodium chloride. Dried with sodium sulfate and evaporated to a thick oil. Purified on a silica gel column eluted with chloroform to provide the title compound. 1H-NMR (CDCl3): 4.0 ppm (s, 2H); 7.1-7.6 ppm (20H); 6.6 ppm(s, 1H).

Provenance & Evidence