Ethyl bromoacetate → (2-Propyl-phenoxy)-acetic Acid Ethyl Ester

HRID 1991148Notes

Reaction equation

HRID 1991148 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH2:2][CH3:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C=O)C.O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:1][CH2:2][CH3:3])[CH3:23]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 125702-Propylphenol

Product 1

HCID 20768112(2-Propyl-phenoxy)-acetic Acid Ethyl EsterYield 103.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Propylphenol (15.0 g, 110 mmol) was dissolved in DMF (70 mL), and stirred at 0° C. To the solution was added K2CO3 (30.43 g, 220.2 mmol) and ethyl 2-bromoacetate (13.43 mL, 121.1 mmol), and the reaction was stirred at room temperature for 3.5 h. The reaction was diluted with water, and the product was extracted with EtOAc twice. The organic layer was washed with water, brine, dried over Na2SO4, and concentrated in vacuo to give residue. The residue was purified using silica gel column chromatography (hexane/EtOAc=30/1) to give 4.2 (25.4 g). 1H NMR (400 MHz) (CDCl3) δ 7.18-7.08 (2H, m); 6.91 (1H, t, J=7.4 Hz); 6.71 (1H, d, J=8.1 Hz); 4.62 (2H, s); 4.25 (2H, q, J=7.1 Hz); 2.68-2.57 (2H, m); 1.70-1.60 (2H, m); 1.29 (3H, t, J=7.1 Hz); 0.95 (3H, t, J=7.4 Hz).

Workup

  1. stirringthe reaction was stirred at room temperature for 3.5 h
  2. extractionthe product was extracted with EtOAc twice
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give residue
  7. customThe residue was purified

Sources & evidence

ORD record
ord-b8abe5c1aa034c17b4b3ef42a713da9d
Source dataset
uspto-grants-2010_01
Patent number
US07645779B2

Reaction notes

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