Reacción #409076

Ecuación de reacción

sodium thiosulfate

sec-BuLi

3-fluoro-(2-(4-propylphenyl)ethyl)benzene

iodine

→

3-fluoro-4-iodo-(2-(4-propylphenyl)ethyl)benzene

Rendimiento 90.2%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawhile being maintained at a temperature lower than −60° C.
2. 2
   workup.STIRRINGthey were stirred at the same temperature for 1 hour
3. 3
   Extracciónextracted with 50 ml of heptane
4. 4
   OtroThe organic layer thus obtained
5. 5
   Lavadowas washed with water thrice
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off under a reduced pressure

Procedimiento

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%)

Fuente