Ethyl bromoacetate → HCID 57361058, compound

HRID 1295463Notes

Reaction equation

HRID 1295463 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1437134-Iodo-2-methylphenol

Product 1

HCID 57361058HCID 57361058, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Iodo-2-methylphenol (3.0 g, 12.9 mmol) was dissolved in acetone (250 ml) at room temperature, and then potassium carbonate (2.67 g, 19.4 mmol, 1.5 eq.) was added thereto and vigorously stirred. Ethyl bromoacetate (1.56 ml, 14.1 mmol, 1.5 eq.) was quickly added to the mixture, and then reacted further at room temperature for 4 hours. After completion of the reaction, the reaction mixture was extracted with aqueous ammonium chloride solution and ethyl acetate, and dried over magnesium sulfate. The crude product was purified on silica flash column. The solvent was evaporated under reduced pressure to thereby yield 4.26 g of the title compound (yield: 98.5%).

Workup

  1. customreacted further at room temperature for 4 hours
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with aqueous ammonium chloride solution and ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified on silica flash column

Sources & evidence

ORD record
ord-f73b4cc8354845f0b4aa805478de3839
Source dataset
uspto-grants-2007_07
Patent number
US07241901B2

Reaction notes

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