1,2-Dibromoethane → Methyl 3-(2-bromoethoxy)benzoate

HRID 491402Notes

Reaction equation

HRID 491402 reaction equation
[Br:1][CH2:2][CH2:3]Br.C(=O)([O-])[O-].[K+].[K+].[OH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]>CC(C)=O>[Br:1][CH2:2][CH2:3][O:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 10491483Methyl 3-(2-bromoethoxy)benzoateYield 37.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 1,2-dibromoethane (15.4 g, TCI) in acetone (50 ml) was added with potassium carbonate (13.6 g), and added dropwise with a solution of methyl 3-hydroxybenzoate (5.0 g, TCI) in acetone (20 ml), and then the mixture was refluxed for 24 hours by heating. The insoluble solid was removed by filtration, and then the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (Flash, hexane:ethyl acetate=3:1) to obtain the title compound (Intermediate id-01, 3.18 g).

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperatureby heating
  3. customThe insoluble solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Flash, hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-2072bd95d2be4e0da7b85f1800b63e18
Source dataset
uspto-grants-2009_05
Patent number
US07531533B2

Reaction notes

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