Azobisisobutyronitrile → 4-Bromocrotonic acid 2,2,2-trichloroethyl ester

HRID 249534Notes

Reaction equation

HRID 249534 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[Cl:21][C:22]([Cl:31])([Cl:30])[CH2:23][O:24][C:25](=[O:29])/[CH:26]=[CH:27]/[CH3:28].C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[Cl:21][C:22]([Cl:30])([Cl:31])[CH2:23][O:24][C:25](=[O:29])/[CH:26]=[CH:27]/[CH2:28][Br:1]

Participants

6

Reactant 4

HCID 6547Azobisisobutyronitrile2×HCID 11439SuccinimideHCID 67184N-bromobutanimide2×HCID 15703159Crotonic acid 2,2,2-trichloroethyl ester

Product 1

HCID 157031604-Bromocrotonic acid 2,2,2-trichloroethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

The bromination reaction takes place in carbon tetrachloride with N-bromosuccinimide and AIBN as radical former. For this purpose, an equimolar amount of ester (i) and 0.45 mole N-bromosuccinimide are mixed with 300 ml. carbon tetrachloride and a spatula tip of AIBN added thereto. The reaction mixture is heated under reflux for 4 hours, subsequently allowed to cool and the precipitated succinimide (0.41 mole; 92% of theory) is filtered off. After distilling off the solvent in a vacuum, the residue is purified by column chromatography using PE/PE (25:1 v/v) as elution agent. The end product obtained is a yellow oil. The yield of 75% of theory. C6H6O2BrCl3 (296.3752 g./mole).

Workup

  1. customThe bromination reaction
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 4 hours
  4. temperatureto cool
  5. distillationAfter distilling off the solvent in a vacuum
  6. customthe residue is purified by column chromatography
  7. washas elution agent
  8. customThe end product obtained

Sources & evidence

ORD record
ord-edbb39d930524b6bba4fb53356744f15
Source dataset
uspto-grants-1993_05
Patent number
US05214195

Reaction notes

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