Azobisisobutyronitrile → 5-(Bromomethyl)benzo[d]oxazole

HRID 911332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911332
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[N:7][C:6]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27249705-Methylbenzoxazole

Produkt 1

HCID 219849815-(Bromomethyl)benzo[d]oxazoleAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Combine 5-methyl-benzoxazole (0.5 g, 3.75 mmol), NBS (0.7 g, 3.93 mmol), AIBN (60 mg, 0.37 mmol), chloroform (10 mL) and reflux for 1 h. Cool the reaction mixture to ambient temperature, dilute with chloroform and wash with water. Dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1 and 7:3) to obtain the title compound as a white solid (0.1 g, 13%).

Aufarbeitung

  1. washwash with water
  2. dry with materialDry the organic extracts over anhydrous Na2SO4
  3. customevaporate the solvent
  4. custompurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1, 4:1 and 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-f646cd2a66ad40a6ad4f41e201119d18
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

Notizen zur Reaktion

Wird geladen…