Phosphorus oxide (P4O10) → 2-Bromo-4-methylbenzonitrile

HRID 564439

Reaktionsgleichung

Reaktionsgleichung von HRID 564439
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]#[N:6]

Komponenten

4

Edukt 2

HCID 14812Phosphorus oxide (P4O10)HCID 2623402-Bromo-4-methylbenzamide

Produkt 1

HCID 8208022-Bromo-4-methylbenzonitrileAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of 2-bromo-4-methylbenzamide (14.8 g, 69.1 mmol) in CHCl3 was added phosphorous pentoxide (24.5 g, 172.8 mmol) and the mixture keep refluxing for 12 h. The reaction was allowed to cool to room temperature, and put into the ice water under the condition of stirring. The organic layer was separated and the aqueous layer was extracted with CHCl3 (150 mL×2). The combined organic phase was washed with brine, and dried over Na2SO4. Evaporation of the solvent afforded the title compound, 2-bromo-4-methylbenzonitrile (13.3 g, 98%). 1H NMR (400 MHz, CDCl3): δ 2.41 (s, 3 H), 7.20 (d, J=8.0 Hz, 1 H), 7.51-7.54 (m, 2 H).

Aufarbeitung

  1. temperaturethe mixture keep refluxing for 12 h
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CHCl3 (150 mL×2)
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-b6583c8a462e4d31a2e5ff9461ca532b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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