반응 #409076

반응 방정식

sodium thiosulfate

sec-BuLi

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

iodine

→

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

수율 90.2%

용매

THF

THF

반응 조건

후처리

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

실험 절차

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%)

출처