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Water → 5-(3-Chlorophenyl)pyridine-3-carboxylic acid

HRID 489606
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 489606
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(#N)C.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>[Cl:11][C:12]1[CH:17]=[C:16]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])[CH:15]=[CH:14][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 887075-Bromonicotinic acidHCID 2734323(3-Chlorophenyl)boronic acid

Produkt 1

HCID 222660635-(3-Chlorophenyl)pyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A three neck flask was charged with 5-bromonicotinic acid (2 g, 9.90 mmol), 3-chlorophenylboronic acid (1.55 g, 9.90 mmol), a 0.4 M solution of sodiumcarbonate in water (37 mL, 14.8 mmol) and Acetonitrile (37 mL). The solution was degassed under vacuum and tetrakistriphenylphoshine Pd(0) (0.57 g, 0.495 mmol) was added and the reaction refluxed overnight under nitrogen. The reaction was cooled to room temperature and filtered through a celite pad. The filtrate was partially evaporated under reduced pressure and the remaining solution acidified to pH=2 with 1N HCl. The resulting solid was collected by filtration and dried under vacuum. 1H NMR [(CD3)2SO]: δ 9.15-9.05 (m, 2H), 8.45 (s, 1H), 7.85 (s, 1H), 7.80-7.65 (m, 1H), 7.60-7.42 (m, 2H).

Aufarbeitung

  1. additionwas added
  2. temperaturethe reaction refluxed overnight under nitrogen
  3. filtrationfiltered through a celite pad
  4. customThe filtrate was partially evaporated under reduced pressure
  5. filtrationThe resulting solid was collected by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0d9fcbec9582485c9c942f724f751c0c
Quelldatensatz
uspto-grants-2005_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06977263B2

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