Ethyl 2-bromopropionate → Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate

HRID 2058073Notes

Reaction equation

HRID 2058073 reaction equation
[Na].[Cl:2][C:3]1[CH:17]=[CH:16][C:6]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Br[CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:11][CH:10]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 43212004-[(4-Chloroanilino)methyl]phenolHCID 5360545Sodium

Product 1

HCID 20329856Ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionateYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.256 g of sodium in 30 ml of ethanol is added 2 g of 4-(4-chloroanilinomethyl)phenol, and 2.02 g of ethyl 2-bromopropionate is further added dropwise at room temperature. The mixture is thereafter refluxed under heating for 5.5 hours. The ethanol is distilled off from the reaction mixture, 20 ml of water is added to the residue, and the diluted residue is extracted with ether. The extract is washed twice with a saturated aqueous solution of sodium chloride and then dried. After distilling off the solvent from the dried extract, the residue (2.9 g) is purified by column chromatography, using 60 g of silica gel and chloroform as a developer, to give 2.1 g of ethyl 2-[4-(4-chloroanilinomethyl)phenoxy]propionate as an oily product.

Workup

  1. additionis further added dropwise at room temperature
  2. temperatureThe mixture is thereafter refluxed
  3. temperatureunder heating for 5.5 hours
  4. distillationThe ethanol is distilled off from the reaction mixture, 20 ml of water
  5. additionis added to the residue
  6. extractionthe diluted residue is extracted with ether
  7. washThe extract is washed twice with a saturated aqueous solution of sodium chloride
  8. customdried
  9. distillationAfter distilling off the solvent from the dried
  10. extractionextract
  11. customthe residue (2.9 g) is purified by column chromatography

Sources & evidence

ORD record
ord-a75bb6201e01496e94f771cf3f624016
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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