Reaktion #1671981

Reaktionsgleichung

N-Bromosuccinimide

1-(7-methyl-benzofuran-5-yl)-1H-tetrazole

→

title compound

5-Tetrazol-1-yl-benzofuran-7-carbaldehyde

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturat reflux
3. 3
   SonstigeThe mixture was evaporated in vacuo
4. 4
   workup.DISSOLUTIONthe solid residue dissolved in acetonitrile (5 ml)
5. 5
   workup.ADDITIONthen added dropwise to a solution of N-methyl morpholine-N-oxide (0.2 g) in acetonitrile (10 ml)
6. 6
   workup.ADDITIONcontaining 4 Å sieves
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent removed in vacuo
9. 9
   Sonstigethe residue purified by FCC
10. 10
    Wascheneluting with ether-hexane (2:1)

Vorschrift

N-Bromosuccinimide (180 mg) was added to a hot solution of 1-(7-methyl-benzofuran-5-yl)-1H-tetrazole and azoisobutyronitrile (35 mg) in carbon tetrachloride (10 ml) and the mixture heated at reflux whilst irradiating with a 60 W tungsten lamp for 4 hours. The mixture was evaporated in vacuo, the solid residue dissolved in acetonitrile (5 ml) then added dropwise to a solution of N-methyl morpholine-N-oxide (0.2 g) in acetonitrile (10 ml) containing 4 Å sieves. The reaction mixture was stirred for 16 h at room temperature, filtered, the solvent removed in vacuo and the residue purified by FCC eluting with ether-hexane (2:1) to give the title compound as a white solid (56 mg) m.p. 174-175°.

Quelle