Benzoyl Peroxide → 4-Bromoethyl-isophthalic acid dimethylester

HRID 397239Notes

Reaction equation

HRID 397239 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1C=CC(C)=C(C(O)=O)[CH:5]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:33]N1C(=O)CCC1=O.C[CH2:42][CH2:43][CH2:44][CH2:45][CH3:46].C[CH2:48][O:49][C:50]([CH3:52])=[O:51]>C(Cl)(Cl)(Cl)Cl>[CH3:48][O:49][C:50](=[O:51])[C:52]1[CH:46]=[CH:45][C:44]([CH2:43][CH2:42][Br:33])=[C:4]([C:3]([O:2][CH3:1])=[O:14])[CH:5]=1

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21226206Ethyl acetate hexaneHCID 229994865-(Methoxycarbonyl)-2-methylbenzoic acid

Product 1

HCID 537536654-Bromoethyl-isophthalic acid dimethylester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of (4) (0.96 g, 4.61 mmol), dibenzoylperoxide (56 mg, 0.23 mmol) and N-bromosuccinimide (NBS) (0.82 g, 4.61 mmol) in carbon tetrachloride (20 ml) was heated at reflux for 20 hours. After cooling to room temperature and filteration the solvent was evaporated to-give a yellow oil. Flash chromatograph: silica, hexane/EtOAc (7:3) afforded the pure compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours
  3. customfilteration the solvent was evaporated
  4. customto-give a yellow oil

Sources & evidence

ORD record
ord-283f7ea7f3c2420ca4ccffc4d3095f59
Source dataset
uspto-grants-2003_08
Patent number
US06610269B1

Reaction notes

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