2-Chloro-6-nitrotoluene → 2-(Bromomethyl)-1-chloro-3-nitrobenzene

HRID 1521662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1521662
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Komponenten

5

Edukt 3

HCID 67402-Chloro-6-nitrotolueneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Produkt 1

HCID 918582-(Bromomethyl)-1-chloro-3-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-chloro-2-methyl-3-nitrobenzene (10 g, 0.0584 mol) in CCl4 (100 mL) was added N-bromosuccinimide (12.4 g, 0.0701 mol), benzoyl peroxide (2.8 g, 0.0116 mol) portion wise at 0° C. Reaction mixture was stirred at reflux for 4 h. The mixture was filtered, concentrated and dried to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ 8.042-7.986 (m, 1H), 7.925-7.905 (d, J=8 Hz, 1H), 7.658-7.617 (t, J=8.4 Hz, 1H), 4.784 (s, 2H).

Aufarbeitung

  1. customReaction mixture
  2. temperatureat reflux for 4 h
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3f26d83ed6db49b99b226227e04012b8
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073929B2

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