Ethyl 2-bromopropionate → HCID 12952829, compound

HRID 263075Notes

Reaction equation

HRID 263075 reaction equation
Br[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1.[Na]>C(O)C>[Cl:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 79040Ethyl 2-bromopropionateHCID 5360545SodiumHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 12952829HCID 12952829, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.9 g (0.115 mol) of ethyl 2-bromo-propionate are run over the course of 30 minutes into a hot solution of 23 g (0.1045 mol) of p-(p-chlorophenoxy)-phenol and 2.4 g (0.1045 mol) of sodium in 90 ml of anhydrous ethanol and the mixture is then heated to the reflux temperature for 2 hours. The inorganic salts are removed by filtration and the ethanol is driven off under reduced pressure. After having dissolved the residue in diethyl ether, washed the solution with water, dried the organic phase over dry sodium sulphate and evaporated the solvent, 32.5 g of an orange-coloured oil which is insoluble in water are obtained.

Workup

  1. temperaturethe mixture is then heated to the reflux temperature for 2 hours
  2. customThe inorganic salts are removed by filtration
  3. dissolutionAfter having dissolved the residue in diethyl ether
  4. washwashed the solution with water
  5. dry with materialdried the organic phase over dry sodium sulphate
  6. customevaporated the solvent, 32.5 g of an orange-coloured oil which
  7. customare obtained

Sources & evidence

ORD record
ord-105ca99adc6e4babaf7ea7d5d5f64915
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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