N,N-Dimethylbenzylamine → 4,4'-Dibromostilbene

HRID 1156252

Reaktionsgleichung

Reaktionsgleichung von HRID 1156252
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=O)=[CH:4][CH:3]=1.[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=C)=[CH:14][CH:13]=1.C(N(C)C)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC=CC=1C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[CH:16][C:15]2[CH:18]=[CH:19][C:12]([Br:11])=[CH:13][CH:14]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7681N,N-DimethylbenzylamineHCID 162634-BromostyreneHCID 685154-Bromobenzoyl chloride

Produkt 1

HCID 533959814,4'-DibromostilbeneAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

0.112 mg (0.5 millimols) of palladium acetate, 10.97 g (50 millimols) of 4-bromobenzoyl chloride, 10.17 g (50 millimols) of 4-bromostyrene and 6.76 g (50 millimols) of N-benzyldimethylamine in 100 m of o-xylene are stirred for 1 hour at 130° C. After having filtered off the amine salt which has precipitated, the filtrate is concentrated and the crude product is recrystallised twice from toluene. 7.8 g (46% of theory) of 4,4'-dibromostilbene are obtained in the form of white flakes; melting point 213.3° C.

Aufarbeitung

  1. filtrationAfter having filtered off the amine salt which
  2. customhas precipitated
  3. concentrationthe filtrate is concentrated
  4. customthe crude product is recrystallised twice from toluene

Quellen und Nachweise

ORD-Eintrag
ord-32cec8b9af47431d904cd532230fa04b
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04335055

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