Reaktion #50546

Reaktionsgleichung

3-Bromothiophenol

acrylonitrile

→

3-[(3-bromophenyl)thio]propionitrile

Ausbeute 93.7%

Lösungsmittel

sodium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTriton B (1 mL) was added, at which time the reaction mixture
2. 2
   Temperaturto reflux
3. 3
   workup.ADDITIONwithout added
4. 4
   Temperaturheat
5. 5
   Extraktionextracted with diethyl ether
6. 6
   SonstigeThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

3-Bromothiophenol (10 g, 52.9 mmmol) was dissolved in acrylonitrile (11.28 g, 213 mmol). Triton B (1 mL) was added, at which time the reaction mixture became exothermic and began to reflux without added heat. The mixture was allowed to cool to room temperature, poured into cold aqueous sodium hydroxide (2%; 200 mL), and extracted with diethyl ether. The organic layer was dried, filtered and evaporated to provide 12 g (93%) of 3-[(3-bromophenyl)thio]propionitrile as a tan oil; 1H NMR (CDCl3) δ7.54 (s, 1H), 7.42 (d, 1H), 7.32 (d, 1H), 7.25-7.15 (m, 2H), 3.15 (t, 2H), 2.62 (t, 2H); Mass spectrum m/z 261, 259 (M+NH4).

Quelle