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

HRID 1060002

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][C:14](B(O)O)=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21].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:14]2[CH:15]=[CH:16][C:11]([CH3:10])=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=2)[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a suspension of 2-bromo-4-methoxypyridine (2.5 g), 4-methyl-3-nitrophenylboronic acid (3.37 g) and tetrakis(triphenylphosphine)-palladium (768 mg) in 1,2-dimethoxyethane (100 ml) was added 2M aqueous solution of sodium carbonate (18.6 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. Methanol was added to the residue. The precipitate was collected by filtration and dried under reduced pressure to give 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (3.09 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
additionMethanol was added to the residue
filtrationThe precipitate was collected by filtration
customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-095fc507c68f4166bbaf3abdc528761d
Quelldatensatz: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06521643B1

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