Benzoyl Peroxide → 4-Bromoethyl-isophthalic acid dimethylester

HRID 2218937Notes

Reaction equation

HRID 2218937 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-6f4713bd9ddb44dd955be17255b13fbc
Source dataset
uspto-grants-2008_08
Patent number
US07413727B2

Reaction notes

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