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Sodium Carbonate → 4-(6-Methylpyridin-2-yl)benzoic acid

HRID 494184
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 494184
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:15]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([OH:17])=[O:16]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:4]1[N:3]=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:15]([OH:17])=[O:16])=[CH:19][CH:20]=2)[CH:7]=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 792052-Bromo-6-methylpyridineHCID 3121834-Carboxyphenylboronic Acid

Produkt 1

HCID 534263364-(6-Methylpyridin-2-yl)benzoic acidAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a stirred, degassed mixture of 2-bromo-6-methylpyridine (3 g, 17 mmol), sodium carbonate (10.8 g, 100 mmol) and 4-carboxybenzeneboronic acid (2.3 g, 14 mmol) in DME (150 ml) and water (150 ml) under an argon atmosphere was added tetrakis(triphenylphosphine) palladium (0) (350 mg) and the mixture heated to reflux for 18 h. On cooling, ˜50% of the solvent was removed in vacuo and the residual aqueous solution was washed with EtOAc, then acidified to pH1 with concentrated HCl and washed with further EtOAc. The aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which was collected by filtration, washed with water and dried to give the title compound as a white solid (2.3 g). MS (ES): MH+ 212.

Aufarbeitung

  1. customTo a stirred, degassed
  2. temperaturethe mixture heated
  3. temperatureto reflux for 18 h
  4. temperatureOn cooling
  5. custom˜50% of the solvent was removed in vacuo
  6. washthe residual aqueous solution was washed with EtOAc
  7. washwashed with further EtOAc
  8. additionThe aqueous was then adjusted to pH 5 by addition of potassium carbonate causing formation of a white precipitate which
  9. filtrationwas collected by filtration
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-982d8bf5dc474d4589f10314da6112be
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07538121B2

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