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

HRID 593533Notes

Reaction equation

HRID 593533 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.[Br:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:14][CH2:13][Br:12])[CH:5]=1

Participants

5

Reactant 3

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

Product 1

HCID 10491483Methyl 3-(2-bromoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A flask is charged with 3-hydroxybenzoic acid methyl ester (2.54 g, 16.0 mmol) and acetone (50 mL). 1,2-Dibromo-ethane (5.69 mL, 66.0 mmol) and potassium carbonate (2.76 g, 19.0 mmol) are added and the mixture is refluxed for 24 h. The reaction mixture is then cooled to room temperature. The solids are filtered off and the filtrate concentrated in vacuo. The residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 3:1) to afford 3-(2-bromo-ethoxy)-benzoic acid methyl ester as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.66 (t, J=6.2 Hz, 2H), 3.93 (s, 3H), 4.35 (t, J=6.2 Hz, 2H), 7.14 (m, 1H) 7.37 (m, 1H) 7.57 (m, 1H) 7.68 (m, 1H).

Workup

  1. temperaturethe mixture is refluxed for 24 h
  2. filtrationThe solids are filtered off
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue is purified by silica gel flash chromatography (heptane-ethyl acetate, 3:1)

Sources & evidence

ORD record
ord-2b413bc8b7ff4df3bd85cc8e1a0efa38
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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