Ethyl bromoacetate → Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate

HRID 2185025Notes

Reaction equation

HRID 2185025 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[Cl:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:6][C:5]=1[Cl:11]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 224594084-(2-Bromoethyl)-3-chlorophenol

Product 1

HCID 12049887Ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-(2-bromoethyl)-3-chlorophenol (158 mg) in acetone (7 ml) were added potassium carbonate (139 mg) and ethyl bromoacetate (89 μl) at room temperature. After the mixture was stirred for 20 hours at room temperature, the insoluble material was filtered off and the filtrate was concentrated in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate 7/1) gave ethyl 2-[4-(2-bromoethyl)-3-chlorophenoxy]acetate (193 mg).

Workup

  1. filtrationthe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate 7/1)

Sources & evidence

ORD record
ord-2f99117a4a784d0b802a708cedd321aa
Source dataset
uspto-grants-2002_06
Patent number
US06399660B1

Reaction notes

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