p-Toluenesulfonic acid → 2-Bromo-6-methoxybenzo[b]thiophene

HRID 1453906

Reaktionsgleichung

Reaktionsgleichung von HRID 1453906
[Br:1]N1C(=O)CCC1=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]2[CH:26]=[CH:27][S:28][C:24]=2[CH:23]=1>ClCCCl>[Br:1][C:27]1[S:28][C:24]2[CH:23]=[C:22]([O:21][CH3:20])[CH:30]=[CH:29][C:25]=2[CH:26]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 67184N-bromobutanimideHCID 136342376-Methoxy-1-benzothiophene

Produkt 1

HCID 235129022-Bromo-6-methoxybenzo[b]thiopheneAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

N-bromosuccinimide (14.70 g, 82.59 mmol) and p-toluenesulfonic acid (2.70 g, 15.68 mmol) were added to a solution of benzothiophene (3) (15.10 g, 92.07 mmol) in 1,2-dichloroethane (300 ml). The mixture was maintained at 70° C. for 35 min, cooled in an ice bath, and the succinimide was removed by filtration. The solution was extracted with saturated sodium bicarbonate solution, dried over Na2SO4, filtered, and concentrated under vacuum to give 22.00 g as an oil. Crystallisation from pentane afforded a white solid (16.50 g, 74%), mp 62° C.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customthe succinimide was removed by filtration
  3. extractionThe solution was extracted with saturated sodium bicarbonate solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give 22.00 g as an oil
  8. customCrystallisation from pentane

Quellen und Nachweise

ORD-Eintrag
ord-77fd94c4c66d4329b9c479b4e8728942
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07476691B2

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