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Water → 3-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile

HRID 1624857
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1624857
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C(=O)N([Br:22])C(=O)C1.O>CN(C=O)C>[Br:22][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH2:11][CH2:12][C:13]#[N:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 3199323-(3,4-Dimethoxyphenyl)propanenitrile

Produkt 1

HCID 3204113-(2-Bromo-4,5-dimethoxyphenyl)propanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1 g (5.3 mmoles) of 3-(3,4-dimethoxyphenyl)propanenitrile in 42 mL of DMF is cooled to 0° C. To the resulting solution there is added, little by little, 0.93 g of NBS (5.2 mmoles, 1 eq.). After stirring for 30 minutes at 0° C., the reaction mixture is brought back to ambient temperature and stirred for two hours. It is then hydrolysed using 170 mL of water and extracted twice with 130 mL of ethyl acetate. The organic phases are collected and then washed, first with saturated aqueous Na2S2O5 solution and then with water. After evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which crystallises into a white solid are obtained.

Aufarbeitung

  1. additionTo the resulting solution there is added
  2. customis brought back to ambient temperature
  3. stirringstirred for two hours
  4. extractionextracted twice with 130 mL of ethyl acetate
  5. customThe organic phases are collected
  6. washwashed, first with saturated aqueous Na2S2O5 solution
  7. customAfter evaporating off the solvent under reduced pressure, 1.29 g of a colourless oil which
  8. customcrystallises into a white solid
  9. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-a655c0a9287149348456602ed37746f2
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08779121B2

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