Hydrochloric Acid → 3-(Trifluoromethoxy)Phenylacetylene

HRID 606809Notes

Reaction equation

HRID 606809 reaction equation
C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)[C:9]#[C:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:21])([F:20])[F:19])[CH:12]=1.Cl>C(O)C>[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]([F:19])([F:20])[F:21])[CH:12]=1)#[CH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67047416Benzene, 1-(trifluoromethoxy)-3-[2-(trimethylsilyl)ethynyl]-

Product 1

HCID 269862623-(Trifluoromethoxy)PhenylacetyleneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add potassium carbonate (257 mg, 1.86 mmol) to a solution of trimethyl-(3-trifluoromethoxyphenylethynyl)-silane (960 mg, 3.72 mmol) in ethanol (15 mL) and stir for 16 h. Add a 10% aqueous solution of hydrochloric acid to neutralize the reaction mixture and then partition between water and hexanes. Separate the organic layer and concentrate with cooling to give the title compound (571.4 mg, 83%).

Workup

  1. custompartition between water and hexanes
  2. customSeparate the organic layer
  3. concentrationconcentrate
  4. temperaturewith cooling

Sources & evidence

ORD record
ord-7a710a28966f41cd81b88439505a9f60
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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