Sodium Carbonate → 2,6-Dibromopyridine

HRID 853764

Reaktionsgleichung

Reaktionsgleichung von HRID 853764
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CO.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>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.[C:9]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

9

Edukt 3

HCID 10340Sodium CarbonateHCID 122742,6-DibromopyridineHCID 66827Phenylboronic Acid

Produkt 3

HCID 122742,6-DibromopyridineHCID 729202,6-DiphenylpyridineHCID 5686792-Bromo-6-phenylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 600 mg (2.5 mmol) of 2,6-dibromopyridine in 15 mL of toluene was added a mixture of 150 mg (1.27 mmol) of phenylboronic acid in 5 mL of methanol, 86 mg (0.075 mmol) of Pd(PPh3)4 and 15 mL of 2 M Na2CO3. The mixture was refluxed overnight, cooled, extracted with ethyl acetate, dried and 2-bromo-6-phenylpyridine isolated chromatographically from unreacted 2,6-dibromopyridine and 2,6-diphenylpyridine.

Aufarbeitung

  1. additionwas added
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled
  4. extractionextracted with ethyl acetate
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3451a2226e724a519ba58f4c3cb38d4d
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07256186B2

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