2-Bromobenzyl bromide → Anthracene

HRID 849384

Reaktionsgleichung

Reaktionsgleichung von HRID 849384
CNC[C:4]1[C:5]2[C:10]([CH:11]=[C:12]3[C:17]=1[CH:16]=[CH:15][CH:14]=[CH:13]3)=[CH:9][CH:8]=[CH:7][CH:6]=2.BrC1C=CC=CC=1CBr>C(#N)C>[CH:6]1[C:5]2[C:10](=[CH:11][C:12]3[C:17]([CH:4]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:8][CH:7]=1

Komponenten

4

Edukt 2

HCID 769652-Bromobenzyl bromideHCID 1881289-(Methylaminomethyl)anthracene

Produkt 1

HCID 8418AnthraceneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 9-((methylamino)methyl)anthracene (1.00 g, 4.5 mmol), 2-bromobenzyl bromide (1.13 g, 4.5 mmol) and K2CO, (0.691 g, 5.0 mmol) in 50 mL of acetonitrile was refluxed under nitrogen for 18 hr. The solution was filtered on a sintered-glass filter and solvent was removed from the filtrate under reduced pressure to yield 9-(N-Methyl-N-(o-bromobenzyl)amino)methyl)anthracene (95% by NMR). The resulting solid was taken up in diethyl ether (50 mL), and treated at 0° C. with 1 equiv of butyllithium. The mixture was stirred at 0° C. for 2 h at which time 5 equiv of trimethyborate was added via a cannula. After warming the mixture to room temperature, 50 mL of water was added to quench the reaction. The ether layer was separated, washed with 3×10 mL water, and dried over sodium sulfate. Removal of the solvent under reduced pressure provided a solid identical to that obtained in (A) in 52% yield.

Aufarbeitung

  1. filtrationThe solution was filtered on a sintered-glass
  2. filtrationfilter
  3. customsolvent was removed from the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3bd005e35bc24f56a5c8a012f7338760
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011984

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