Iodine → HCID 18513409, compound

Participants

Reaction Conditions

Reaction Steps

In a solution of 4.8 g (19.7 mmol) of the 3-fluoro-(2-(4-propylphenyl)ethyl)benzene obtained in the previous step in 25 ml of THF was added dropwise 23 ml of sec-BuLi (1.04 M, cyclohexane solution, corresponding to 23.7 mmol) while being maintained at a temperature lower than −60° C., and they were stirred at the same temperature for 1 hour. Subsequently, a solution of 7.5 g (29.6 mmol) of iodine in 20 ml of THF was added dropwise to the reaction mixture while being maintained at a temperature lower than −60° C., and they were stirred at the same temperature for 1 hour. The reaction solution was poured into 50 ml of a diluted aqueous sodium thiosulfate solution, and extracted with 50 ml of heptane. The organic layer thus obtained was washed with water thrice and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under a reduced pressure, the residue was subjected to silica gel column chromatography (eluent: heptane) to obtain 6.5 g of a crude 3-fluoro-4-iodo-(2-(4-propylphenyl)ethyl)benzene. This product was used for next reaction without any further purification. (Yield: 90.2%)

Provenance & Evidence