Sodium Carbonate → 2-(4-Methoxypyridin-2-yl)toluene

HRID 1059959

Reaktionsgleichung

Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH3:10])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of 2-bromo-4-methoxypyridine (1.88 g), 2-methylphenylboronic acid (1.77 g) and tetrakis(triphenylphosphine)-palladium (578 mg) in 1,2-dimethoxyethane (30 ml) was added 2M aqueous solution of sodium carbonate (13 ml). The mixture was stirred at 80° C. for 7 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane) to give 2-(4-methoxypyridin-2-yl)toluene (1.98 g).

Aufarbeitung

temperaturecooled to room temperature
customThe organic layer was separated
washwashed with water and brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane)

Quellen und Nachweise

ORD-Eintrag: ord-a305d08f1e5542e1b07a3b2fb5615217
Quelldatensatz: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06521643B1

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