Reaction #334233

Reaction equation

4-Methoxythiophenol

bromochloromethane

triethylamine

→

1-Chloromethylthio-4-methoxybenzene

Conditions

Workup

1. 1
   Temperatureexternal cooling
2. 2
   Otherthe reaction below room temperature
3. 3
   workup.ADDITIONOnce the addition
4. 4
   workup.STIRRINGwas stirred at room temperature for 1 h
5. 5
   WashThe mixture was then washed with water
6. 6
   Dryingthe organic solution dried (MgSO4)
7. 7
   Otherthe solvent evaporated off
8. 8
   workup.DISTILLATIONthe residue distilled

Procedure

4-Methoxythiophenol (40 mmol) was dissolved in bromochloromethane (0.8 mol) and triethylamine (40 mmol) added dropwise with stirring and external cooling to keep the reaction below room temperature. Once the addition was completed the reaction mixture was stirred at room temperature for 1 h. The mixture was then washed with water, the organic solution dried (MgSO4), the solvent evaporated off and the residue distilled; yield: 3.90 g (52%), b.p. 70° C./0.01 mmHg. The physical data for the title compound are detailed in J. Hayami, N. Tanaka, S. Kurabayashi, Y. Kotani and A. Kaji; Bull.Chem.Soc. (Japan) 44, 3091 (1971).

Source