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Sodium Carbonate → [1,1':2',1''-Terphenyl]-2-amine

HRID 348584
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 348584
Br[C:2]1[CH:8]=[CH:7][CH:6]=[C:5](Br)[C:3]=1[NH2:4].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.CCOCC.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>[C:2]1([C:11]2[C:10]([C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=3)=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 3

HCID 10340Sodium Carbonate2×HCID 66827Phenylboronic AcidHCID 690982,6-Dibromoaniline

Produkt 1

HCID 12595497[1,1':2',1''-Terphenyl]-2-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2,6-Dibromoaniline (6.02 g, 24 mmol) and Pd(PPh3)4 (3.88 g, 3.00 mmol) were dissolved in toluene (240 ml). Phenyl boronic acid (8.80 g, 72 mmol) in EtOH (50 ml) was added. Na2CO3 (13 g, 144 mmol) in H2O (70 ml) was added. The reaction mixture was reflux for 24 hrs. The organic layer was thin separated and the amine precipitated as hydrochloride salt by addition of 20 ml of HCl. The precipitate was isolated. The salt was suspended in ether, and 2 M Na2CO3 was added. The organic layer was dried over Na2SO4 and the solvent was evaporated. The yield was 90%. 1H NMR (CDCl3): δ 7.44 (t, 4H, Harom), 7.39 (t, 4H, Harom), 7.29 (d, 2H, Harom), 7.07 (d, 2H, Harom), 6.82 (t, 1H, Harom), 3.77 (s, 2H, NH2).

Aufarbeitung

  1. temperatureThe reaction mixture was reflux for 24 hrs
  2. customThe organic layer was thin separated
  3. customthe amine precipitated as hydrochloride salt by addition of 20 ml of HCl
  4. customThe precipitate was isolated
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-32f1229f4af7448c84f5f11bab7404b8
Quelldatensatz
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07176950B2

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