Potassium Carbonate → HCID 90403129, compound

HRID 2200613Notes

Reaction equation

HRID 2200613 reaction equation
BrC[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[F:10][C:11]([F:21])([F:20])[O:12][C:13]1[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:10][C:11]([F:20])([F:21])[O:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 27332613-(Trifluoromethoxy)phenol

Product 1

HCID 90403129HCID 90403129, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 4-bromobutanoate (2 g, 10.26 mmol) in acetone (20 mL) was added 3-(trifluoromethoxy)phenol (1.52 g, 8.54 mmol), followed by potassium carbonate (3.5 g, 25.36 mmol). The reaction was stirred at room temperature overnight. The mixture was partitioned between DCM and water. The organic phase was washed with brine, dried over sodium sulfate, and concentrated to give a crude product which was purified by silica gel chromatography eluting with petroleum/ethyl acetate (10:1 to 5:1) to give ethyl 3-(3-(trifluoromethoxy)phenoxy)propanoate (2.3 g, 92.1% yield) as a colorless oil.

Workup

  1. customThe mixture was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a crude product which
  6. customwas purified by silica gel chromatography
  7. washeluting with petroleum/ethyl acetate (10:1 to 5:1)

Sources & evidence

ORD record
ord-80c027458933456fbef00b690c9ebcc8
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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