N-bromobutanimide → Methyl 3-(bromomethyl)-4-chlorobenzoate

HRID 2414259Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2414259
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 7015786Benzoic acid, 4-chloro-3-methyl-, methyl ester

Produkt 1

HCID 12144656Methyl 3-(bromomethyl)-4-chlorobenzoateAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6547AzobisisobutyronitrileKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

40.4 g of methyl 4-chloro-3-methylbenzoate, 39 g of N-bromosuccinimide and 1 g of azobisisobutyronitrile were added to 300 ml of carbon tetrachloride, followed by reflux under heating for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, insoluble matters were collected by filtration and the filtrate was concentrated. The obtained crude crystals were washed with hexane to obtain 34.3 g of methyl 3-bromomethyl-4-chlorobenzoate as white crystals.

Aufarbeitung

  1. temperatureby reflux
  2. temperatureunder heating for 4 hours
  3. customAfter completion of the reaction
  4. filtrationinsoluble matters were collected by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe obtained crude crystals
  7. washwere washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-ced7b1884ccd4a3685a8f5369d7bdf31
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06812229B1

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