Potassium Carbonate → 1-Bromo-3-ethynylbenzene

HRID 2240981

Reaktionsgleichung

Reaktionsgleichung von HRID 2240981
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([C:14]#[C:15][Si](C)(C)C)[CH:11]=[CH:12][CH:13]=1>CO>[Br:7][C:8]1[CH:9]=[C:10]([C:14]#[CH:15])[CH:11]=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 3683324((3-Bromophenyl)ethynyl)trimethylsilane

Produkt 1

HCID 114808181-Bromo-3-ethynylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To each of 2 one-liter flasks were charged K2CO3 (68 g, 493 mmol), a large magnetic stirbar and MeOH (250 mL). Stirring was begun on both reaction mixtures and once it was satisfied that they were stirring without any problems, 3-bromophenyltrimethylsilylacetylene (12.5 g, 49.3 mmol, 10.5 mL) was added to each reaction vessel and the mixtures were refluxed overnight. The reaction mixtures were filtered and the filter cakes were washed with MeOH. The combined filtrate was concentrated in vacuo, diluted with hexanes, and washed with water twice. The organic layer was concentrated to give a yellow oil. Flash chromatography (SiO2, Hexanes), provided 9.1 g, 50%, of the title compound as a colorless to light yellow oil. 1H NMR 500 MHz (CDCl3) δ 3.08 (s, 1H); 7.16 (t, 1H, J=7.89 Hz); 7.38 (dt, 1H, J=7.77 Hz, 2.44 Hz); 7.44-7.47 (m, 1H); 7.61 (t, 1H, J=1.68 Hz).

Aufarbeitung

  1. customwas begun on both reaction mixtures and once it
  2. additionwas added to each reaction vessel
  3. temperaturethe mixtures were refluxed overnight
  4. customThe reaction mixtures
  5. filtrationwere filtered
  6. washthe filter cakes were washed with MeOH
  7. concentrationThe combined filtrate was concentrated in vacuo
  8. additiondiluted with hexanes
  9. washwashed with water twice
  10. concentrationThe organic layer was concentrated
  11. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-09ca21e5e3024d969bbb3a9ff72b3184
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723368B2

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