Triethylamine → Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoate

HRID 541737

Reaktionsgleichung

Reaktionsgleichung von HRID 541737
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.Cl.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.[Cu]I>[N+:12]([C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])([O-:14])=[O:13]

Komponenten

9

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 239341Methyl 3-bromo-5-nitrobenzoate

Produkt 1

HCID 57961569Methyl 3-nitro-5-[(trimethylsilyl)ethynyl]benzoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl 3-bromo-5-nitrobenzoate (0.331 g, 1.27 mmol), (trimethylsilyl)acetylene (0.27 mL, 1.9 mmol), bis(triphenylphosphine)palladium(II) chloride (45 mg, 0.064 mmol), copper(I) iodide (19 mg, 0.10 mmol) and triethylamine (0.26 mL, 1.9 mol) in DMF (5 mL) was stirred at room temperature overnight. The solution was diluted with ethyl acetate and 1 N HCl. The aqueous layer was extracted with ethyl acetate once, and the combined organic solutions were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the desired product (310 mg, 88%). LCMS for C13H16NO4Si (M+H)+: m/z=278.1.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with ethyl acetate once
  2. washthe combined organic solutions were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-67d343bf7e1b4022b90e0219bb2f0e9a
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

Verknüpfte Notizen

Wird geladen…