Reaction #50577

Reaction equation

chloroacetonitrile

2,3-dichloro-thiophenol

sodium methanolate

→

2,3-dichloro-phenylthioacetonitrile

Yield 59.1%

Solvents

methanol

Conditions

Workup

1. 1
   workup.ADDITIONare added in portions
2. 2
   Temperaturewith cooling
3. 3
   workup.STIRRINGthe mixture is stirred for 2 hours at room temperature and for a further 5 hours
4. 4
   Temperatureat reflux temperature
5. 5
   FiltrationThe entire batch is then filtered while hot and
6. 6
   Concentrationconcentrated in vacuo

Procedure

15.0 g (83.8 mmol) of 2,3-dichloro-thiophenol are introduced into 50 ml of absolute methanol, 4.5 g (83.8 mmol) of sodium methanolate are added in portions, with cooling, and the mixture is stirred for 15 minutes at room temperature. 6.3 g (83.8 mmol) of chloroacetonitrile are subsequently added dropwise, and the mixture is stirred for 2 hours at room temperature and for a further 5 hours at reflux temperature. The entire batch is then filtered while hot and concentrated in vacuo. 10.8 g (59.1% of theory) of 2,3-dichloro-phenylthioacetonitrile are obtained.

Source