N-bromobutanimide → 2-Azido-1-(bromomethyl)-4-iodobenzene

HRID 1869753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869753
[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH3:11])=[N+:2]=[N-:3].[Br:12]N1C(=O)CCC1=O>C1C=CC=CC=1>[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:12])=[N+:2]=[N-:3]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 579875492-Azido-4-iodo-1-methylbenzene

Produkt 1

HCID 579873052-Azido-1-(bromomethyl)-4-iodobenzeneAusbeute 67,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of the azide from step 1 (9.1 g, 0.035M), N-Bromosuccinimide (6.8 g, 0.039M) and 1,1azobis(cyclohexanecarbonitrile) (0.85 g, 3.5 mmol) in benzene (40 ml) was heated at reflux overnight. The solvent was evaporated under vacuum and the residue was diluted EtOAc (100 ml) and washed with water (50 ml) and brine, dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography (silica, hexanes) to give the azide as a white solid (8 g, 67%). 1H NMR (500 MHz, CDCl3): δ 4.30 (2H, s), 6.98 (1H, d, J 8.0), 7.35 (2H, t, J 7.0).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated under vacuum
  4. washwashed with water (50 ml) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography (silica, hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2712c556c46f4892a5de18991fb307c6
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638629B2

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