Water → HCID 67119286, compound

HRID 2076577Notes

Reaction equation

HRID 2076577 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[I:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.O>CN(C)C=O>[I:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:8][C:9]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:10]=2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 67119147HCID 67119147, compound

Product 1

HCID 67119286HCID 67119286, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.30 g, 9.41 mmol) was added to a solution of tert-butyl 2-(bromomethyl)-5-(trifluoromethyl)benzoate (2.00 g, 5.90 mmol) obtained in Example (2-2) and 4-iodophenol (1.30 g, 5.91 mmol) in N,N-dimethylformamide (20 ml) under ice-cooling and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate (three times). After the organic layer was successively washed with water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1-50/1) to give tert-butyl 2-[(4-iodophenoxy)methyl]-5-(trifluoromethyl)benzoate as a colorless solid (2.65 g, yield: 94%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (three times)
  3. washAfter the organic layer was successively washed with water (three times)
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate, it
  5. concentrationwas concentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=100/1-50/1)

Sources & evidence

ORD record
ord-6cb7491a8a834d3480bd3e4c8f31bccf
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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