Ethyl bromoacetate → Ethyl 2-(5-chloro-2-methoxyphenoxy)acetate

HRID 1862610Notes

Reaction equation

HRID 1862610 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([CH:7]=1)[O:8][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 588774Phenol, 5-chloro-2-methoxy-

Product 1

HCID 18620157Ethyl 2-(5-chloro-2-methoxyphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-chloro-2-methoxyphenol (488 mg) in acetone (15 ml) were added cesium carbonate (1.20 g) and ethyl bromoacetate (375 μl), and the mixture was stirred for 1 hour at room temperature. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Purification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=6/1) gave ethyl 2-(5-chloro-2-methoxyphenoxy)acetate (572 mg).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification of the residue by flash column chromatography on silica gel (eluent: hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-6bb59a5168c14f8da619c4cdbac83b5c
Source dataset
uspto-grants-2003_03
Patent number
US06538152B1

Reaction notes

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