N-bromobutanimide → 5-(Bromomethyl)-2-chlorobenzonitrile

HRID 1709662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1709662
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([CH2:10][Br:11])=[CH:6][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 125572002-Chloro-5-methylbenzonitrile

Produkt 1

HCID 140330355-(Bromomethyl)-2-chlorobenzonitrileAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-5-methylbenzonitrile (10.6 g, 69.9 mmol), N-bromosuccinimide (12.2 g, 68.5 mmol), and dibenzoyl peroxide (349 mg, 1.44 mmol) in benzene (350 ml) was refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was suspended in 7:3 (v/v) hexane-dichloromethane, filtered, and evaporated. The crude product was chromatographed on silica gel (650 g) eluted with 7:3 (v/v) hexane-dichloromethane to provide 4.8 g (30%) 4-chloro-3-cyanobenzyl bromide, m.p. 55°-58° C.

Aufarbeitung

  1. temperaturewas refluxed 1.5 hours
  2. temperaturecooled
  3. customevaporated to dryness under vacuum
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel (650 g)
  7. washeluted with 7:3 (v/v) hexane-dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a87c250ef91449c1ba95a28514ddbcab
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04950673

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