4-Iodo-1-tritylimidazole → (4-Cyano-3-fluorophenyl)[1-(triphenylmethyl)imidazol-4-yl]methanol

Participants

Reaction Steps

To a solution of 4-iodo-1-(triphenylmethyl)imidazole (2.93 g, 6.71 mmol) in dry CH2Cl2 (30 mL), under argon, was added MeMgBr (2.35 mL of a 3.0M solution in Et2O, 7.05 mmol), dropwise. The resulting solution was stirred at ambient temperature for 1 hour, then transferred dropwise into a stirred solution of 4-cyano-3-fluorobenzaldehyde, as described in Example 11, Step B, (1.00 g, 6.71 mmol) in dry THF (30 mL), under argon, at −78° C. After 30 min, the reaction mixture was quenched with saturated aqueous NH4Cl (50 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with EtOAc to yield the desired alcohol as a white solid.

Provenance & Evidence