Benzoyl Peroxide → 2-Bromomethyl-3-chloro-benzoic acid methyl ester

HRID 915355Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915355
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH3:11].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH2:11][Br:13]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5077673Methyl 3-chloro-2-methylbenzoate

Produkt 1

HCID 110327262-Bromomethyl-3-chloro-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a suspension of 3-chloro-2-methylbenzoic acid methyl ester (5.62 g, 30.4 mmol), and N-bromosuccinimide (5.94 g, 33.4 mmol) in carbon tetrachloride (200 mL) was added benzoyl peroxide (800 mg, 3.30 mmol). The resulting suspension was immersed in an oil bath held at 85° C., and illuminated with a 300W halogen worklight. After stirring for 16 hours with heat and illumination the reaction mixture was allowed to cool to ambient temperature, filtered to remove the insoluble succinimide, and concentrated under reduced pressure to afford 2-bromomethyl-3-chlorobenzoic acid methyl ester as a yellow semi-solid. This crude material was carried on to the next step without purification.

Aufarbeitung

  1. customThe resulting suspension was immersed in an oil bath
  2. customheld at 85° C.
  3. temperaturewith heat
  4. filtrationfiltered
  5. customto remove the insoluble succinimide
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b56bee1961144b4aa3ff7812de85e48
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265131B2

Notizen zur Reaktion

Wird geladen…