Potassium Carbonate → 1-Bromo-3-ethynylbenzene

HRID 2241011Notes

Reaction equation

HRID 2241011 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:13]=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=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 two 1 L flasks was charged K2CO3 (68 g, 493.7 mmol), a large magnetic stirbar, and MeOH (250 mL). Stirring was begun and once the reaction mixtures were stirring without any problems, ((3-bromophenyl)ethynyl)trimethylsilane (12.5 g, 49.4 mmol, 10.5 mL) was added to each reaction vessel and the reaction mixtures were refluxed overnight. The cooled reaction mixtures were filtered and the filter cake was washed with MeOH. The filtrate was diluted with water and washed with Hexanes (at least 500 mL) three times. The combined organic layers were concentrated to give a yellow oil that was absorbed onto 50 g Celite. Flash chromatography (SiO2, Hexanes) provided 9.1 g, 50%, of the title compound as a colorless to light yellow oil.

Workup

  1. customonce the reaction mixtures
  2. additionwas added to each reaction vessel
  3. customthe reaction mixtures
  4. temperaturewere refluxed overnight
  5. customThe cooled reaction mixtures
  6. filtrationwere filtered
  7. washthe filter cake was washed with MeOH
  8. additionThe filtrate was diluted with water
  9. washwashed with Hexanes (at least 500 mL) three times
  10. concentrationThe combined organic layers were concentrated
  11. customto give a yellow oil that
  12. customwas absorbed onto 50 g Celite
  13. customFlash chromatography (SiO2, Hexanes) provided 9.1 g, 50%

Sources & evidence

ORD record
ord-4096468fab4741e886983f5b74b278da
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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