Potassium Carbonate → Methyl 2-(4-acetyl-2-bromophenoxy)acetate

HRID 68597

Reaction equation

HRID 68597 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:13][C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:9]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:2]([Br:1])[CH:3]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanone

Product 1

HCID 66868355Methyl 2-(4-acetyl-2-bromophenoxy)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-bromo-4-hydroxyphenyl)ethanone (15) (963 mg, 4.48 mmol, 1 eq, Aldrich, Milwaukee, Wis., USA) in DMF (15 mL), was added methyl 2-bromoacetate (1.02 g, 6.72 mmol, 1.5 eq) and potassium carbonate (1.86 g, 13.5 mmol; 3 eq). The reaction mixture was stirred at room temperature for 18 h. Solvent was removed in vacuo, and the residue was dissolved in EtOAc, washed by water and brine, dried (Na2SO4), filtered, and concentrated in vacuo to give 1.05 g, (81%) of methyl 2-(4-acetyl-2-bromophenoxy)acetate (16) as a brown solid.

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed by water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53bed643add440ce9aa0f42a890cfb39
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Linked notes

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