N,N-Dimethylbenzylamine → 4-Bromocinnamonitrile

HRID 1156477

Reaktionsgleichung

Reaktionsgleichung von HRID 1156477
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.[C:11](#[N:14])[CH:12]=C.C(N(C)C)C1C=CC=CC=1>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[CH:12][C:11]#[N:14])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7681N,N-DimethylbenzylamineHCID 7855AcrylonitrileHCID 685154-Bromobenzoyl chloride

Produkt 1

HCID 534804-BromocinnamonitrileAusbeute 67,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7809P-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

54.88 g (0.25 mol) of 4-bromobenzoyl chloride, 20.81 ml (0.31 mol) of acrylonitrile and 37.65 ml (0.25 mol) of N-benzyldimethylamine are added to 0.561 g (2.5 millimols) of palladium acetate in 500 ml of p-xylene. The mixture is stirred for 1.5 hours at 120° C. The crude product is distilled and recrystallised from cyclohexanone. 35 g (67% of theory) of 4-bromocinnamonitrile are obtained in the form of white flakes; melting point 105.7° C. Analysis for C9H4NBr: calculated C 51.96%, H 2.91%, N 6.73%, Br 38.40%; found C 51.93%, H 3.01%, N 6.69%, Br 38.35%.

Aufarbeitung

  1. distillationThe crude product is distilled
  2. customrecrystallised from cyclohexanone

Quellen und Nachweise

ORD-Eintrag
ord-97bbf48433274827836567a26694ad0a
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04335054

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