Water → 5-[2-(3-Bromopropoxy)ethyl]-1-benzothiophene

HRID 7462

Reaktionsgleichung

Reaktionsgleichung von HRID 7462
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15]O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37].O>C(Cl)Cl>[Br:37][CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[S:1][CH:2]=[CH:3][C:4]=2[CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 219900663-[2-(1-Benzothiophen-5-yl)ethoxy]-1-propanol

Produkt 1

HCID 219900765-[2-(3-Bromopropoxy)ethyl]-1-benzothiopheneAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwas added to the solution
  2. temperatureunder ice-cooling
  3. customthe organic layer was separated
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. additionDiethyl ether was added to the residue
  9. filtrationthe insoluble materials were filtered off
  10. distillationafter which the solvent was distilled off under reduced pressure
  11. customThe residue was purified by a column chromatography (eluent; hexane:ethyl acetate=20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-955645a8fc6a4fd1b0144ff9ec621f18
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087594B2

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