Hydrochloric Acid → 5-Chlorobenzo[b]thiophene-3-methanol

HRID 1785826

Reaktionsgleichung

Reaktionsgleichung von HRID 1785826
Br[CH2:2][C:3]1[C:7]2[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:6]=2[S:5][CH:4]=1.C([O-])(=[O:15])C.[K+].Cl>[OH-].[Na+].O1CCOCC1>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]2[S:5][CH:4]=[C:3]([CH2:2][OH:15])[C:7]=2[CH:8]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 517044Potassium AcetateHCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Produkt 1

HCID 27761365-Chlorobenzo[b]thiophene-3-methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 3-bromomethyl-5-chlorobenzothiophene (2.5 g, 9.56 mmol) and potassium acetate (1.96 g, 20 mmol) in 1M NaOH (40 mL) and dioxane (40 mL) was heated to reflux for 24 hours, adjusted to pH<7with 1M HCl, and extracted with ethyl acetate (3×). The combined extracts were washed with brine, concentrated, and purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

Aufarbeitung

  1. temperatureto reflux for 24 hours
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with brine
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bf503cb461c64ebc88b8beab3808c3c6
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504512B2

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