Benzoyl Peroxide → (E)-4-bromo-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19265Notes

Reaction equation

HRID 19265 reaction equation
[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)\[CH3:7])[CH3:2].[Br:17]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)\[CH2:7][Br:17])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66894928(E)-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester

Product 1

HCID 66893436(E)-4-bromo-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl esterYield 64.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred mixture of (E)-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester (3.45 g, 0.014 mol) in carbon tetrachloride (20 mL) under a nitrogen atmosphere was added N-bromosuccinimide (2.79 g, 0.016 mol) and benzoyl peroxide (347 mg, 0.001 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the resulting mixture was heated to reflux for 4 h. The reaction mixture was then placed in the refrigerator overnight. The solids formed were removed by filtration and the filtrate concentrated in vacuo. The crude product obtained was purified using flash column chromatography (silica gel (100-200 mesh), ethyl acetate/hexanes) to afford (E)-4-bromo-3-(3-chloro-phenoxy)-but-2-enoic acid ethyl ester (2.90 g, 63%) as a yellow oil.

Workup

  1. customNitrogen gas was bubbled through the mixture for 5 min
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 h
  4. customwas then placed in the refrigerator overnight
  5. customThe solids formed
  6. customwere removed by filtration
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product obtained
  9. customwas purified

Sources & evidence

ORD record
ord-14811994013f4996bd30b1ce42a7a9e9
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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