Reaktion #1856385

Reaktionsgleichung

2-(4-methylphenyl)-3-cyanothiophene

N-bromosuccinimide

→

2-(4-bromomethylphenyl)-3-cyanothiophene

Ausbeute 67.1%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas irradiated with UV light for one hour
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Filtrationthe solid filtered off
4. 4
   EinengenThe filtrate was concentrated
5. 5
   Sonstigethe residue purified by flash chromatography
6. 6
   Wascheneluting with 5% ethyl acetate/hexane

Vorschrift

A mixture of 2-(4-methylphenyl)-3-cyanothiophene (1.5 g, 7.5 mmol), N-bromosuccinimide (1.34 g, 7.5 mmol), and azabicyclononane (20 mg) in carbon tetrachloride was irradiated with UV light for one hour. The reaction mixture was cooled, and the solid filtered off. The filtrate was concentrated, and the residue purified by flash chromatography, eluting with 5% ethyl acetate/hexane, to yield 2-(4-bromomethylphenyl)-3-cyanothiophene 1.4 g, m.p. 68-75 (slightly impure, used as such).

Quelle