N-bromobutanimide → 2-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzene

HRID 225991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 225991
[CH3:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 81171alpha,alpha,alpha-Trifluoro-3-nitro-o-xylene

Produkt 1

HCID 106781242-(Bromomethyl)-1-nitro-3-(trifluoromethyl)benzeneAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-1-nitro-3-trifluoromethyl-benzene (5.0 g, 24.4 mmol) in CCl4 (300 mL) was added N-bromosuccinimide (4.35 g, 24.4 mmol) and benzoyl peroxide (0.11 g, 0.45 mmol). The mixture was heated to reflux and exposed to light (300 W) for 20 h. The mixture was cooled to room temperature, filtered and concentrated. Purification by column chromatography (EtOAc-hexanes) afforded 3.03 g (44%) of the benzyl bromide, a yellow oil. 1H NMR (400 MHz, CDCl3) δ 4.93 (s, 2 H), 7.63 (t, J=8.1 Hz, 1 H), 7.94 (d, J=7.8 Hz, 1 H), 8.06 (d, J=8.1 Hz, 1 H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-82a5997e89054bbc8d02b3cb53adfcc0
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557135B2

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