Hydrochloric Acid → 3,7-Dibromodibenzo(b,d)thiophene

HRID 2095457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095457
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]3[CH:16]=[CH:17][C:18]([Br:20])=[CH:19][C:14]=3[S:13](=O)(=O)[C:12]=2[CH:23]=1.CCOCC.Cl>C(Cl)(Cl)Cl.O>[Br:20][C:18]1[CH:17]=[CH:16][C:15]2[C:11]3[CH:10]=[CH:9][C:8]([Br:7])=[CH:23][C:12]=3[S:13][C:14]=2[CH:19]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 40718983,7-Dibromo-dibenzothiophene 5,5-dioxideHCID 21226445Aluminium lithium hydride2×

Produkt 1

HCID 8037593,7-Dibromodibenzo(b,d)thiopheneAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (4.1 g) is slowly introduced in small amounts over 50 minutes, in an ice bath, into a mixture of 3,7-dibromodibenzothiophene dioxide (20 g) and anhydrous ether (200 ml) in a 500-ml flask, and the mixture is heated to reflux and stirred for 2 hours. Water (200 ml) is added thereto to deactivate lithium aluminum hydride, and chloroform (200 ml) and concentrated hydrochloric acid (40 ml) are added to the mixture. The resulting mixture is thoroughly stirred, and the organic layer is separated. The aqueous layer is further extracted with chloroform (200 ml×2), and the extract is combined with the organic layer. The combined organic layer is washed with water (200 ml) and saturated brine (200 ml), and is dried over calcium chloride. The solvent is distilled off, and colorless crystals thus obtained are recrystallized from ethyl acetate+ethanol (16:3). Thus, 8.8 g of 3,7-dibromodibenzothiophene is obtained.

Aufarbeitung

  1. temperaturethe mixture is heated
  2. temperatureto reflux
  3. additionare added to the mixture
  4. stirringThe resulting mixture is thoroughly stirred
  5. customthe organic layer is separated
  6. extractionThe aqueous layer is further extracted with chloroform (200 ml×2)
  7. washThe combined organic layer is washed with water (200 ml) and saturated brine (200 ml)
  8. dry with materialis dried over calcium chloride
  9. distillationThe solvent is distilled off
  10. customcolorless crystals thus obtained
  11. customare recrystallized from ethyl acetate+ethanol (16:3)

Quellen und Nachweise

ORD-Eintrag
ord-6722264f6fb54c5586c7caf7d6811fc0
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445900B2

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