1,2-Dimethoxyethane → 4-(4-Methoxyphenyl)pyridine

HRID 1107286

Reaktionsgleichung

Reaktionsgleichung von HRID 1107286
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl.Br[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(COC)OC.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C1(P(CCCC[Pd-](Cl)Cl)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 6038134-(4-Methoxyphenyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479790HCID 178479790, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-methoxybenzene boronic acid (2 g, 13.15 mmol), 4-bromopyridine hydrochloride (3.84 g, 19.72 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 1.5 hours under a nitrogen atmosphere. The solution was allowed to cool to ambient temperature, diluted with ethyl acetate (150 ml) and washed with water (150 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate and the solvents were removed leaving a white solid, which was chromatographed on silica gel in 70-100% ethyl acetate/hexane giving the title compound as a white solid (1.95 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.66-8.63 (2H, d, J=6.2 Hz), 7.63-7.59 (2H, d, J=9.0 Hz), 7.50-7.47 (2H, d, J=6.2 Hz), 7.03-6.99 (2H, d, J=9.0 Hz), and 3.87 (3H, s). m/z (ES+) 186 (M+1).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. washwashed with water (150 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. customthe solvents were removed
  6. customleaving a white solid, which
  7. customwas chromatographed on silica gel in 70-100% ethyl acetate/hexane giving the title compound as a white solid (1.95 g, 80%)

Quellen und Nachweise

ORD-Eintrag
ord-9a6730cc97d14ccdb48d0726af1da283
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06060469

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