Sodium Carbonate → 2-Amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrile

HRID 52626

Reaktionsgleichung

Reaktionsgleichung von HRID 52626
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5].[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([Cl:19])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:15]2[CH:14]=[C:13]([Cl:12])[CH:18]=[C:17]([Cl:19])[CH:16]=2)=[C:6]([Cl:11])[C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 27343313,5-Dichlorophenylboronic acidHCID 543850846-Amino-3-bromo-2-chlorobenzonitrile

Produkt 1

HCID 541017212-Amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrileAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

This compound was prepared in a manner analogous to that of Step D of Example 1, using 2.3 grams (0.010 mole) of 2-amino-5-bromo-6-chlorobenzonitrile (prepared as in Step A of Example 2), 2.9 grams (0.015 mole) of 3,5-dichlorophenylboronic acid, 0.1 gram (catalyst) of tetrakis(triphenylphosphine)palladium(0), and 30 mL of aqueous 2M sodium carbonate in 75 mL of toluene. The solid product was recrystallized from toluene, yielding 1.9 grams of 2-amino-6-chloro-5-(3,5-dichlorophenyl)benzonitrile. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. customThis compound was prepared in a manner analogous to that of Step D of Example 1
  2. customThe solid product was recrystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-0d644f32164c41a88910cfe52f7390a7
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616718

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