9-Bromomethylanthracene → 9-(Azidomethyl)anthracene

HRID 910709

Reaktionsgleichung

Reaktionsgleichung von HRID 910709
Br[CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C)C=O>[N:17]([CH2:2][C:3]1[C:4]2[C:9]([CH:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N+:18]=[N-:19]

Komponenten

4

Edukt 2

HCID 170199-BromomethylanthraceneHCID 33557Sodium Azide

Produkt 1

HCID 43899719-(Azidomethyl)anthraceneAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 9-bromomethyl-anthracene (7.85 g, 29.0 mmol) and sodium azide (7.79 g, 120 mmol) in dimethylformamide (DMF, 190 mL) was heated at 50° C. for 30 minutes. The mixture was cooled to room temperature, and extracted with ether, and the ether layers were washed with water, dried over MgSO4 and concentrated to give 9-azidomethyl-anthracene as yellow crystals (5.92 g, 87% yield). 1H NMR (CDCl3) δ 8.53 (1H, s), 8.31 (2H, d), 8.07 (2H, d), 7.61 (2H, dd), 7.53 (2H, dd), 5.35 (2H, s).

Aufarbeitung

  1. extractionextracted with ether
  2. washthe ether layers were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-35486c1e1d5641ce960f9d5bcbf059e6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022214B2

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