Benzoyl Peroxide → 4-(Bromomethyl)-3-chlorobenzonitrile

HRID 67865

Reaktionsgleichung

Reaktionsgleichung von HRID 67865
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[CH2:10][Br:11]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 888943-Chloro-p-toluonitrile

Produkt 1

HCID 130420934-(Bromomethyl)-3-chlorobenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 3-chloro-4-methyl-benzonitrile (30.0 g, 0.2 mol), N-bromosuccinimide (36.0 g, 0.21 mol) and benzoyl peroxide (100 mg) in 600 mL of CCl4 was refluxed with illumination for 72 h. N-Bromosuccinimide (5.0 g) was added and the reaction was continued for an additional 24 h. The mixture was cooled, filtered and evaporated. Recrystallization from heptane gave pure 2-chloro-4-cyanobenzyl bromide: yield 24.5 g; mp 83°-85° C. Anal. calcd for C8H5BrClN; C, 41.69; H, 2.19; N, 6.07. Found: C, 41.48; H, 1.80; N, 5.76. ##STR27##

Aufarbeitung

  1. temperaturewas refluxed with illumination for 72 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated
  5. customRecrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-e36a76c8198e44b5994e1489848c4c62
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04347177

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