Imidazole → Methyl 4-(4-fluorophenyl)-4-iodobutanoate

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenylphosphine (419 mg, 1.6 mmol) in anhydrous 20 mL DCM was added imidazole (224 mg, 3.3 mmol) and iodine (406 mg, 1.6 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then methyl 4-(4-fluorophenyl)-4-hydroxybutanoate (212 mg, 1 mmol) in 10 mL DCM was added to the mixture. The resulting mixture was stirred at 0° C. for 2 h and the temperature was slowly raised to room temp over a period of 3 h. Evaporation of solvent left the crude product as an oil from which the product was isolated by Flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give the title compound, 161 mg, as a light yellow oil.

Provenance & Evidence