3-Methylbut-1-yne → 4-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

HRID 40130

Reaktionsgleichung

Reaktionsgleichung von HRID 40130
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][CH:14]([CH3:17])[C:15]#[CH:16]>CCN(CC)CC.CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][CH:14]([CH3:17])[CH3:13])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

Komponenten

7

Edukt 2

HCID 690193-Methylbut-1-yneHCID 2926594-Iodo-3-nitroanisole

Produkt 1

HCID 597623514-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (Aldrich, 10 g, 35.8 mmol) in Et3N (60 ml) and DMF (6 ml) was added CuI (34 mg, 0.18 mmol), Pd(PPh3)2Cl2 (126 mg, 0.18 mmol), and 3-methyl-1-butyne (5.0 ml, 73.5 mmol). The mixture was stirred at room temperature for 16 h and was concentrated. The resulting mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes) to yield the title compound as a brown oil.

Aufarbeitung

  1. concentrationwas concentrated
  2. additionThe resulting mixture was diluted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-b7a226b1c835495eaf8a21b6a00f0eb4
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524917B2

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