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

HRID 869424
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 869424
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

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

Produkt 1

HCID 867222712-(4-Chloro-2-methoxycarbonyl-phenyl)-2-bromo-acetic acid methyl esterAusbeute 120,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943
Carbon Tetrachloride
Lösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cfb59e5d069f4e4f98143453397b206c
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969373B2

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