Benzyl Bromide → 1-Benzyl-1H-benzotriazole

HRID 1371038

Reaktionsgleichung

Reaktionsgleichung von HRID 1371038
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.CC([O-])(C)C.[K+].C1COCC1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.O>[CH2:21]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

7

Edukt 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 23665647Potassium tert-butoxideHCID 178418385HCID 178418385, Verbindung

Produkt 1

HCID 5212121-Benzyl-1H-benzotriazoleAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of benzotriazole (1.2 g, 10.1 mmol) in DMF (40 mL) at r.t. was added a solution of 1M KOtBu in THF (11 mL, 11 mmol). After stirring for 30 min., benzyl bromide (2.0 g, 11.6 mmol) was added. The mixture was further stirred for 1 h, diluted with H2O, and extracted with EtOAc. The EtOAc extract was washed with H2O (3×), dried (MgSO4) and concentrated. The residue was stirred with hexane containing small amount of Et2O to give 1.2 g (57%) of the title compound as a white powder.

Aufarbeitung

  1. stirringThe mixture was further stirred for 1 h
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with H2O (3×)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. stirringThe residue was stirred with hexane containing small amount of Et2O

Quellen und Nachweise

ORD-Eintrag
ord-90d48bbc411049d29c20e14239b06e74
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583126B2

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