Ammonia → 2-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthalene

HRID 1433853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433853
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.C([Sn](CCCC)(CCCC)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[N+:27]([O-:29])=[O:28])CCC.[Cl-].[Li+].N>CS(C)=O.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.[Cu]Cl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=3[N+:27]([O-:29])=[O:28])[CH:9]=2)[CH:4]=1

Komponenten

9

Edukt 4

HCID 222AmmoniaHCID 787862-Bromo-6-methoxynaphthaleneHCID 433294Lithium ChlorideHCID 23087474Tributyl(4-methoxy-2-nitrophenyl)tin

Produkt 1

HCID 230875562-Methoxy-6-(4-methoxy-2-nitrophenyl)naphthaleneAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 62652Cuprous chlorideKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The title compound was synthesized by referring to J. Am. Chem. Soc., 1999, 121, 760. A suspension of 6-methoxy-2-bromonaphthalene (500 mg), tributyl(4-methoxy-2-nitrophenyl)tin (1.1 g), tetrakis(triphenylphosphine)palladium(0) (250 mg), copper(I) chloride (1.0 g) and lithium chloride (540 mg) in dimethylsulfoxide (15 ml) was stirred at 60° C. for 5 hours under a nitrogen atmosphere. Ethyl acetate and aqueous ammonia were sequentially added thereto, the solution was filtered through celite pad, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was washed with a hexane-diethyl ether system to provide the title compound (412 mg).

Aufarbeitung

  1. customThe title compound was synthesized
  2. filtrationthe solution was filtered through celite pad
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. washThe residue was washed with a hexane-diethyl ether system

Quellen und Nachweise

ORD-Eintrag
ord-8387e951015b4c6db75044133ccf01bd
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612114B2

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