Bromotrichloromethane → 3,5-Diacetoxybromobenzene

HRID 1163275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163275
SC1C=CC=C[N+]=1[O-].[C:9]([O:12][C:13]1[CH:14]=[C:15]([CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)C(Cl)=O)(=[O:11])[CH3:10].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:38]C(Cl)(Cl)Cl>>[C:9]([O:12][C:13]1[CH:14]=[C:15]([Br:38])[CH:19]=[C:20]([O:22][C:23](=[O:25])[CH3:24])[CH:21]=1)(=[O:11])[CH3:10]

Komponenten

5

Edukt 4

HCID 6383BromotrichloromethaneHCID 6547AzobisisobutyronitrileHCID 11368883(3-Acetyloxy-5-carbonochloridoylphenyl) acetateHCID 178526253HCID 178526253, Verbindung

Produkt 1

HCID 686482403,5-DiacetoxybromobenzeneAusbeute 58 %

Versuchsvorschrift

2.6 g (17.5 mmol) 2-mercaptopyridine-1-oxid was dissolved in 30.0 ml bromotrichloromethane and heated to reflux. A mixture of 4.04 g (15 mmol) 3,5-diacetoxybenzoylchloride and 433 mg (2.5 mmol) 2,2′-azobisisobutyronitril dissolved in 30.0 ml bromotrichlioromethane were added dropwise at the same temperature. After additional 2 hours of refluxing the reaction mixture was cooled to room temperature and concentrated in vacuum. Chromatographic purification over silica gel employing a 9:1 (v/v) mixture of n-hexane and ethyl acetate as eluting agent yielded 2.4 g of 3,5-diacetoxybromobenzene (8.7 mmol, 58%).

Aufarbeitung

  1. temperatureheated to reflux
  2. dissolutiondissolved in 30.0 ml bromotrichlioromethane
  3. additionwere added dropwise at the same temperature
  4. temperatureAfter additional 2 hours of refluxing the reaction mixture
  5. concentrationconcentrated in vacuum
  6. customChromatographic purification over silica gel employing
  7. additiona 9:1 (v/v) mixture of n-hexane and ethyl acetate
  8. washas eluting agent

Quellen und Nachweise

ORD-Eintrag
ord-4ab4561fae984b73a6af7f7733b9416b
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820848B2

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