Trimethylsilylacetylene → Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoate

HRID 456871Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456871
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][C:5]=1[Cl:11].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>C(N(CC)CC)C.Cl[Pd-2](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)I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:7]=[CH:6][C:5]=1[Cl:11]

Komponenten

7

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 35563912Methyl 2-chloro-5-iodobenzoate

Produkt 1

HCID 57422929Methyl 2-chloro-5-((trimethylsilyl)ethynyl)benzoateAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 83717Copper iodideKatalysatorHCID 178418903HCID 178418903, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-iodo-benzoic acid methyl ester (3.5 g, 12 mmol), dichlorobis(triphenylphosphino)palladium(II) (0.04 g, 0.06 mmol), triphenylphosphine (0.06 g, 0.24 mmol), copper iodide (0.05 g, 0.24 mmol), (trimethylsilyl)acetylene (1.9 g, 19.2 mmol) in triethylamine (40 mL) was heated at reflux for 12 h. The mixture was concentrated in vacuo, diluted with ethyl acetate (150 mL) and washed sequentially with 10% aqueous citric acid, water, and brine. The organic solution was dried, filtered and concentrated in vacuo to afford the title compound (3.14 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. concentrationThe mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate (150 mL)
  5. washwashed sequentially with 10% aqueous citric acid, water, and brine
  6. customThe organic solution was dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-35f1d8e447844d7bb99c7c89a2e4d1d5
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186742B2

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