Potassium Carbonate → Benzene, 1-chloro-4-ethynyl-

HRID 247822Notes

Reaction equation

HRID 247822 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][Si](C)(C)C)=[CH:10][CH:9]=1>CO>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[CH:15])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 3337298(4-Chlorophenylethynyl)trimethylsilane

Product 1

HCID 70118Benzene, 1-chloro-4-ethynyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous potassium carbonate (0.9g, 0.0065 moles) was added to a solution of chloro-4-trimethylsilylethynylbenzene (3.Og, 0.014 moles) in methanol (60 cm3) under an atmosphere of nitrogen. The reaction was stirred, under nitrogen, at room temperature for 4 hours. The solvent was removed, the solid residue was tritura&ed with ether and then dichloromethane and filtered. The organic filtrates were combined and evaporated to dryness giving chloro-4-ethynylbenzene as a brown solid. This was used in the next step without any further purification yield 1.1 g (58%). 1H NMR 67.3 (2H, d), 7.4 (2H, d), 3.1 (1H, s)ppm.

Workup

  1. customThe solvent was removed
  2. filtrationdichloromethane and filtered
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-b2dde32b2daa4aa9a7ad714a99242910
Source dataset
uspto-grants-1993_05
Patent number
US05208239

Reaction notes

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