Potassium Carbonate → 1-Bromo-3-ethynylbenzene

HRID 2240981

Reaction equation

HRID 2240981 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 114808181-Bromo-3-ethynylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-09ca21e5e3024d969bbb3a9ff72b3184
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Linked notes

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