Ethyl bromoacetate → Ethyl 2-(4-bromophenoxy)acetate

HRID 263071Notes

Reaction equation

HRID 263071 reaction equation
[Na].[CH:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Br:9])[CH:3]=1.Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C.C(OCC)C>[Br:9][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 78084-BromophenolHCID 5360545Sodium

Product 1

HCID 248825Ethyl 2-(4-bromophenoxy)acetate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2.76 g of sodium are dissolved in 100 ml of anhydrous ethanol and 20.8 g (0.120 mol) of p-bromophenol are added. 22.1 g (0.132 mol) of ethyl bromoacetate are run into this solution over the course of 20 minutes and the mixture is then heated under reflux for 1 hour. The ethanol is driven off under reduced pressure and the residue is dissolved in diethyl ether; after washing with water and then with a potassium carbonate solution, and evaporating the solvent, 30.2 g of a white powder are obtained. After purification of this product by crystallisation from petroleum ether, 23 g of a white, water-insoluble powder are obtained.

Workup

  1. customare run into this solution over the course of 20 minutes
  2. temperaturethe mixture is then heated
  3. temperatureunder reflux for 1 hour
  4. washafter washing with water
  5. customwith a potassium carbonate solution, and evaporating the solvent, 30.2 g of a white powder
  6. customare obtained
  7. customAfter purification of this product
  8. customby crystallisation from petroleum ether, 23 g of a white, water-insoluble powder
  9. customare obtained

Sources & evidence

ORD record
ord-54eda809368045afbe124a2693625d1a
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

Loading…