1,1-Dibromoethane → 2-Fluoro-4-(1-trityl-1h-imidazol-4-ylmethyl)-benzonitrile

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Reaction Steps

Zinc (0.301 g, 4.63 mmol) and dibromoethane (0.040 mL, 0.463 mmol) were stirred in anhydrous THF (2 mL) under Ar for 1.5 h. A solution of 4-bromomethyl-2-fluoro-benzonitrile (as described in Example 1, Step D) (0.546 g, 2.55 mmol) in anhydrous THF (1 mL) was added dropwise and stirred for 1 h. A mixture of 4-iodo-1-trityl-1H-imidazole (0.808 g, 1.85 mmol) and NiCl2 (PPh3)2 (0.120 g, 0.183 mmol) were added together to the reaction. After stirring overnight under Ar, the reaction was quenched with NH4Cl (9 mL), stirred for 2 h, extracted with CH2Cl2 (3×), dried (MgSO4), concentrated and purified using SiO2 chromatography (0.5% MeOH/CH2Cl2 w/NH4OH) to give the title compound.

Provenance & Evidence