Boron tribromide → 1-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

HRID 510825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510825
[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([O:11]C)=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:3]([CH3:16])=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 27576391-(5-Chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone

Produkt 1

HCID 27576081-(5-chloro-2-hydroxy-4-methyl-3-nitrophenyl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a mixture of 1-(5-chloro-2-methoxy-4-methyl-3-nitrophenyl)ethanone (8.9 g, 37 mmol, from Oakwood) in methylene chloride (200 mL) was added 1.0 M boron tribromide in methylene chloride (38.4 mL, 38.4 mmol) at −78° C. After stirring at −78° C. for 10 minutes, the reaction was allowed to warm up to 0° C., quenched with water at 0° C., and extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and filtered. After evaporating to dryness under reduced pressure, the residue was used directly in next step (8.2 g, 98%). LCMS calculated for C9H9ClNO4 (M+H)+: m/z=230.0. found: 230.1.

Aufarbeitung

  1. temperatureto warm up to 0° C.
  2. customquenched with water at 0° C.
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customAfter evaporating to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fbfaa6712b7c473e897042a074ae24ed
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096600B2

Notizen zur Reaktion

Wird geladen…