Benzoyl Peroxide → 2-(4-Chloro-2-methoxycarbonyl-phenyl)-2-bromo-acetic acid methyl ester

HRID 869424Notes

Reaction equation

HRID 869424 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12]([O:14][CH3:15])=[O:13].C1C(=O)N([Br:24])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[C:12]([O:14][CH3:15])=[O:13])[Br:24]

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimide2×HCID 128996554-Chloro-2-methoxycarbonyl-phenyl acetic acid methyl ester

Product 1

HCID 867222712-(4-Chloro-2-methoxycarbonyl-phenyl)-2-bromo-acetic acid methyl esterYield 120.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

18E (16.48 mmol) was dissolved in CCl4 (50 mL), and was added NBS (N-bromosuccinimide, 3.23 g, 18.13 mmol), followed by catalytic amount of BPO (benzoyl peroxide). The reaction mixture was refluxed for about 20 hours under stirring. When no more product was produced any more, the reaction mixture was cooled and filtered. To the filtrate was added NBS (1.6 g, 8.24 mmol) and catalytic amount of BPO. The reaction mixture was refluxed for additional 10 hours. After the reaction completed, the mixture was cooled and filtered. The filtrate was concentrated to give 6.4 g of a crude product (19A), which was used directly for the next step.

Workup

  1. temperatureThe reaction mixture was refluxed for about 20 hours
  2. customWhen no more product was produced any more, the reaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered
  5. temperatureThe reaction mixture was refluxed for additional 10 hours
  6. temperaturethe mixture was cooled
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-cfb59e5d069f4e4f98143453397b206c
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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