Sodium Carbonate → 3-(4-methylphenyl)pyridine

HRID 1242551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242551
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.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>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)[CH:13]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 79799Tolylboronic acid

Produkt 1

HCID 41331893-(4-methylphenyl)pyridineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 4-tolylboronic acid (38 g, 0.28 mol), 3-bromopyridine (44 g, 0.28 mol), Na2CO3 (200 g) in toluene (500 ml) and water (500 ml) was added Pd(PPh3)4 (16 g, 0.014 mol), and refluxed for 16 h. The reaction mixture was cooled, and the separated organic layer was washed with water and brine, and dried. The solvent was removed to give 4-(3-pyridyl)toluene (42 g, 90%).

Aufarbeitung

  1. temperaturerefluxed for 16 h
  2. temperatureThe reaction mixture was cooled
  3. washthe separated organic layer was washed with water and brine
  4. customdried
  5. customThe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-205602a03e254aa1b48177bb8d017770
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115639B2

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