تفاعل #7558

معادلة التفاعل

water

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

triphenylphosphine

carbon tetrabromide

→

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

المردود 76.2%

المذيبات

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر