Potassium Carbonate → 1-Ethynyl-3-(trifluoromethyl)benzene

HRID 508828Notes

Reaction equation

HRID 508828 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

Product 1

HCID 27784901-Ethynyl-3-(trifluoromethyl)benzeneYield 142.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of trimethyl((3-(trifluoromethyl)phenyl)ethynyl)silane (0.500 g, 2.06 mmol) in ethanol (10 mL) was added potassium carbonate (0.253 g, 1.8 mmol) and the reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with dil. HCl and extracted with hexane and concentrated to afford 0.200 g of the crude product which was further purified by column chromatography using silica (60-120 mesh) eluting with pet. ether to afford 0.500 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 4.41 (s, 1H), 7.64 (d, J=7.5 Hz, 1H), 7.77-7.81 (m, 3H).

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with hexane
  3. concentrationconcentrated
  4. customto afford 0.200 g of the crude product which
  5. customwas further purified by column chromatography
  6. washeluting with pet. ether

Sources & evidence

ORD record
ord-d9c25503165c4bbf86de75c231c59820
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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