Boron tribromide → 1-[2-Hydroxy-4-(methylthio)phenyl]ethanone

HRID 39030Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39030
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16]>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 13578023Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-

Produkt 1

HCID 668786661-[2-Hydroxy-4-(methylthio)phenyl]ethanoneAusbeute 97,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Boron tribromide (19 ml, 1 N in DCM, 19 mmol) was added to a mixture of crude 1-[2-methoxy-4-(methylthio)phenyl]ethanone (3.6 g, 16.9 mmol) and DCM (25 ml) at 0° C. The mixture was brought to room temperature and stirred for 3 h. Ice/water was added, the organic phase was separated and the water phase was extracted with EtOAc. The combined organic phases were filtered through a short plug of silica (EtOAc) and were concentrated to give the title compound (3.0 g) MS m/z (rel. intensity, 70 eV) 183 (6), 182 (M+, 53), 168 (10), 167 (bp), 152 (6).

Aufarbeitung

  1. customwas brought to room temperature
  2. customthe organic phase was separated
  3. extractionthe water phase was extracted with EtOAc
  4. filtrationThe combined organic phases were filtered through a short plug of silica (EtOAc)
  5. concentrationwere concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7243f6522fda490f90dfef429367cc2e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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