N-bromobutanimide → 2-Bromomethyl-5-chloro-4-nitrobenzonitrile

HRID 1739835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739835
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C1C(=O)N([Br:21])C(=O)C1>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:10][C:5]1[CH:4]=[C:3]([N+:11]([O-:13])=[O:12])[C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8]

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimide2×HCID 102417995-Chloro-2-methyl-4-nitrobenzonitrile

Produkt 1

HCID 154289152-Bromomethyl-5-chloro-4-nitrobenzonitrileAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysator2×HCID 7964ChlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 5-chloro-4-nitro-2-methylbenzonitrile (32.0 g, 0.16 mol), NBS (54.0 g, 0.30 mol) and benzoyl peroxide (200 mg, catalytic amount) in chlorobenzene was heated at 130° C. and irradiated with a sunlamp for 15 h. More NBS (30.0 g, 0.17 mol) and benzoyl peroxide (200 mg) were added. The mixture was further reacted for 24 h. After cooling, the precipitate formed was filtered off and washed with CH2Cl2. The combined filtrates were washed with H2O (2×), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was then chromatographed over silica gel and eluted with hexanes:EtOAc (9:1) to give 2-bromomethyl-5-chloro-4-nitrobenzonitrile (48 g, contaminated with starting material and dibrominated product) as a pale yellow solid.

Aufarbeitung

  1. customirradiated with a sunlamp for 15 h
  2. customThe mixture was further reacted for 24 h
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with CH2Cl2
  7. washThe combined filtrates were washed with H2O (2×)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was then chromatographed over silica gel
  11. washeluted with hexanes:EtOAc (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-154b6c551aee4eeaa57aabc2ee6bcb65
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05968958

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