Water → 3-Bromobenzamide

HRID 347667

Reaktionsgleichung

Reaktionsgleichung von HRID 347667
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[OH2:10]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]([NH2:6])=[O:10]

Komponenten

4

Edukt 2

HCID 962Water2×HCID 233813-Bromobenzonitrile

Produkt 1

HCID 898073-BromobenzamideAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-bromobenzonitrile (0.91 g, 5 mmol) in dioxane (19 mL), NaBO3.4H2O (2.12 g, 13.78 mmol) and H2O (19 mL) were added. The mixture was stirred at 80° C. 16 hours (h), cooled, added of H2O and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and evaporated. Purification of the residue by column chromatography (hexane/EtOAc 2:8) and recrystallization gave the desired product as colorless tablets. Yield 80% (EtOH). Mp: 156–7° C. (lit. 156° C.) (Pearson, D. E. et al., J. Org. Chem., 28: 3147–3149, (1963)). MS (EI): m/z 199 (M+); 183 (100%).

Aufarbeitung

  1. temperature16 hours (h), cooled
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. customPurification of the residue
  6. customby column chromatography (hexane/EtOAc 2:8) and recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-e1cdeceb7dc34f52869aa74648684cc2
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176201B2

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