3,5-Dimethylchlorobenzene → 1-(Bromomethyl)-3-chloro-5-methylbenzene

HRID 426122

Reaktionsgleichung

Reaktionsgleichung von HRID 426122
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.[W]>[Br:10][CH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Cl:1])[CH:3]=1

Komponenten

5

Edukt 2

HCID 328873,5-DimethylchlorobenzeneHCID 67184N-bromobutanimide

Produkt 1

HCID 123755491-(Bromomethyl)-3-chloro-5-methylbenzeneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23964TungstenKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

The mixture of 1-Chloro-3,5-dimethyl-benzene (32 g, 0.23 mol) and N-bromosuccinimide (40.5 g, 0.23M) in carbon tetrachloride (400 ml) was refluxed for 3 hr under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, hexane) to afford 33 g (68%) of a white solid. 1H NMR (200 MHz, CDCl3) δ: 2.32 (3H, s), 4.39 (2H, s), 7.10 (2H, s), 7.18 (1H, s).

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4fa415f113bc427290a74a36b5a339d3
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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