반응 #7558

반응 방정식

water

3-[2-(1-benzothiophen-5-yl)ethoxy]-1-propanol

triphenylphosphine

carbon tetrabromide

→

5-[2-(3-bromopropoxy)ethyl]-1-benzothiophene

수율 76.2%

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONwas added to the solution
2. 2
   온도under ice-cooling
3. 3
   기타the organic layer was separated
4. 4
   세척The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
5. 5
   건조a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONdistilled under reduced pressure
7. 7
   기타to remove the solvent
8. 8
   workup.ADDITIONDiethyl ether was added to the residue
9. 9
   여과the insoluble materials were filtered off
10. 10
    workup.DISTILLATIONafter which the solvent was distilled off under reduced pressure
11. 11
    기타The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=20:1 to 10:1)

실험 절차

In 40 mL of methylene chloride was dissolved 2.00 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]-1-propanol, and 5.55 g of triphenylphosphine was added to the solution, after which a solution of 8.42 g of carbon tetrabromide in 10 mL of methylene chloride was added dropwise thereto under ice-cooling and the resulting mixture was stirred at room temperature for 20 minutes. To the reaction mixture was added 20 mL of water, and the organic layer was separated. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Diethyl ether was added to the residue and the insoluble materials were filtered off, after which the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=20:1 to 10:1) to obtain 1.93 g of 5-[2-(3-bromopropoxy)ethyl]-1-benzothiophene as a colorless oil.

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