1,3-Dibromo-5,5-dimethylhydantoin → 1-Bromo-3-(bromomethyl)-5-methylbenzene

HRID 564445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564445
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH2:9][Br:10])[CH:3]=1

Komponenten

5

Edukt 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 136357Benzene, 1-bromo-3,5-dimethyl-

Produkt 1

HCID 223242611-Bromo-3-(bromomethyl)-5-methylbenzeneAusbeute 249,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 1-bromo-3,5-dimethylbenzene (25.0 g, 135.0 mmol) in CCl4 (150 mL), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (14.5 g, 54.0 mmol) and dibenzoyl peroxide (BPO) (0.2 g) were added and the mixture was refluxed for 7 h. After the reaction was cooled to room temperature, the precipitate was filtered though Celite, and then the solid was rinsed two times with pentane (50 mL). The combined filtrate was washed with water (50 mL), followed by saturated sodium bicarbonate (50 mL) and sodium thiosulfate (50 mL×2). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the compound 1-bromo-3-(bromomethyl)-5-methylbenzene (35.6 g, 99%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 7 h
  2. filtrationthe precipitate was filtered though Celite
  3. washthe solid was rinsed two times with pentane (50 mL)
  4. washThe combined filtrate was washed with water (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-0b606b00766a4a7d87c25244b9fe744b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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