2,3-Dichloropyridine → 4-(3-Chloropyridin-2-yl)benzoic acid

HRID 1391429

Reaktionsgleichung

Reaktionsgleichung von HRID 1391429
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)([OH:3])=[O:2].Cl[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][N:15]=1>C([O-])([O-])=O.[K+].[K+].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.[Pd]>[Cl:20][C:19]1[C:14]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[N:15][CH:16]=[CH:17][CH:18]=1

Komponenten

6

Edukt 2

HCID 169882,3-DichloropyridineHCID 27339852-(Dihydroxyboranyl)benzoic acid

Produkt 1

HCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178527696HCID 178527696, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Tetrakis palladium (0.1 2 g, 0.1 mMol) was added to a suspension of carboxybenzene boronic acid (0.33 g, 2.0 mMol) and 2,3-dichloropyridine (0.296 g, 2.0 mMol) in a mixture of 0.4M K2CO3 (10 mL) and acetonitrile (10 mL) and the mixture was heated at 90° C. for 12 hrs under a blanket of nitrogen. The hot suspension was filtered, the filtrate concentrated to about half the original volume before being washed with methylene chloride. The aq. layer was carefully acidified with conc. HCl and the precipitate was collected, washed with water and vacuum dried to obtain the product as a white solid.

Aufarbeitung

  1. filtrationThe hot suspension was filtered
  2. concentrationthe filtrate concentrated to about half the original volume
  3. washbefore being washed with methylene chloride
  4. customthe precipitate was collected
  5. washwashed with water and vacuum
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-64fd27ecb3c84abc97072bb50d7e3fc8
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07338950B2

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