Dichloromethane → 4-Bromo-2-(bromomethyl)-1-chlorobenzene

HRID 576998

Reaktionsgleichung

Reaktionsgleichung von HRID 576998
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH3:9])[CH:3]=1.[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.ClCCl>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][Br:10])[CH:3]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 6098995-Bromo-2-chlorotoluene

Produkt 1

HCID 115582804-Bromo-2-(bromomethyl)-1-chlorobenzeneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-1-chloro-2-methylbenzene (5.0 g, 24.0 mmol), N-bromosuccinimide (4.4 g, 25.0 mmol), and benzoyl peroxide (700 mg, 2.9 mmol) in anhydrous carbon tetrachloride (85 mL) was stirred at reflux for 4 hours. Dichloromethane (50 mL) was added. The mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% EtOAc/hexanes), affording 4-bromo-2-(bromomethyl)-1-chlorobenzene (4.76 g, 70% yield). The product was used without further purification.

Aufarbeitung

  1. temperatureat reflux for 4 hours
  2. extractionThe mixture was extracted with 1 N NaOH (1×150 mL) and brine (1×150 mL)
  3. extractionThe organic extract
  4. customwas recovered
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried in vacuo
  9. customThe crude product was purified by flash chromatography (0-5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4f13da1817c04854b6bdc7ea6c2fc23c
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040538B2

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