N-bromobutanimide → 1-(Bromomethyl)-4-methoxy-2-nitrobenzene

HRID 1678709

Reaktionsgleichung

Reaktionsgleichung von HRID 1678709
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 871374-Methyl-3-nitroanisole

Produkt 1

HCID 37478301-(Bromomethyl)-4-methoxy-2-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

4-Methyl-3-nitroanisole (2.7 mL; manufactured by Sigma-Aldrich Co.) was dissolved in carbon tetrachloride (20 mL; manufactured by Wako Pure Chemical Industries, Ltd.), and NBS (4.0520 g; manufactured by Tokyo Chemical Industry Co., Ltd.) and hydrated benzoyl peroxide (348 mg; manufactured by Sigma-Aldrich Co.) were added to the solution. The mixture was purged with nitrogen, and was stirred for 3 hours at reflux. The reaction solution was filtered, and then the filtrate was washed with an aqueous solution of NaHSO3 and water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=94:6→73:27). Thus, the title compound (3.2549 g) was obtained.

Aufarbeitung

  1. customThe mixture was purged with nitrogen
  2. temperatureat reflux
  3. filtrationThe reaction solution was filtered
  4. washthe filtrate was washed with an aqueous solution of NaHSO3 and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=94:6→73:27)

Quellen und Nachweise

ORD-Eintrag
ord-160003e9764547afa9c7eb3bf7cabab0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008506B2

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