Potassium Carbonate → 3-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamine

HRID 931003

Reaction equation

HRID 931003 reaction equation
[Br:1][C:2]1[C:3]([C:13]#[C:14][Si](C)(C)C)=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[C:3]([C:13]#[CH:14])=[C:4]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[NH2:5]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 575462013-Bromo-5-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

Product 1

HCID 575460303-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamineYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)aniline (2.70 g) in methanol (30 mL) was added potassium carbonate (1.11 g), and the mixture was stirred overnight at room temperature. The solvent was evaporated under reduced pressure, to the residue was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous ammonium chloride solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.56 g).

Workup

  1. customThe solvent was evaporated under reduced pressure, to the residue
  2. additionwas added saturated aqueous ammonium chloride solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous ammonium chloride solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d500e91c93514259ac59da004a617a7a
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Linked notes

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